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b. C. H. Heathcock, R. A. Badger, and J. W. Patterson, Jr., I. Am. Chern. Soc. 89, 4133 (1967). c. C. R. Hauser and W. R. Dunnavant, Org. Synth. 40, 38, (1960). d. G. Opitz, H. Milderberger, and H. Suhr, Iustus Liebigs Ann. Chern. 649, 47 (1961). e. K. Shimo, S. Wakamatsu, and T. Inoiie, I. Org. Chern. 26, 4868 (1961). f. T. A. Spencer, K. K. Schmiegel, and K. L. Williamson, I. Am. Chern. Soc. 85, 3785 (1963).

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b. S. J. Etheredge, I. Org. Chern. 31, 1990 (1966). c. R. Deghenghi and R. Gaudry, Tetrahedron Lett., 489 (1962). d. P. A. Grieco and C. C. Pogonowski, I. Am. Chern. Soc. 95, 3071 (1973). e. E. M. Kaiser, W. G. Kenyon, and C. R. Hauser, Org. Synth. V, 559 (1973).

14. W. G. Kofron and L. G. Wideman, I. Org. Chern. 37, 555 (1972). 15. M. S. Newman, V. DeVries, and R. Darlak, I. Org. Chern. 31, 2171 (1966). 16. H. D. Zook, W. L. Kelly, and I. Y. Posey, I. Org. Chern. 33, 3477 (1968). 17. M. E. Kuehne, I. Org. Chern. 35,171 (1970).

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74,4223 (1952). 4a. W. A. Mosher and R. W. Soeder, l. Org. Chern. 36, 1561 (1971).

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7. G. Stork, S. D. Darling, I. T. Harrison, and P. S. Wharton, l. Arn. Chern. Soc. 84,2018 (1962). 8. Text references 45-47 (pp. 59 and 62). 9a. W. G. Dauben and J. Ipaktschi, l. Arn. Chern. Soc. 95, 5088 (1973).

b. T. J. Curphey and H. L. Kim, Tetrahedron Lett., 1441 (1968). 10. E. Vedejs, K. A. J. Snoble, and P. L. Fuchs, l. Org. Chern. 38,1178 (1973). 11. K. P. Singh and L. Mandell, Chern. Ber. 96, 2485 (1963). 12a. _W. S. Wadsworth, Jr., and W. D. Emmons, l. Arn. Chern. Soc. 83,1733 (1960).

b. D. Seyferth, S. O. Grim, and T. O. Read, l. Arn. Chern. Soc. 83,1617 (1961). c. M. Engelhardt, H. Plieninger, and P. Schreiber, Chern. Ber. 97,1713 (1964). d. K. W. Ratts and R. D. Partos, l. Arn. Chern. Soc. 91, 6112 (1969).

13. E. E. Schweizer and G. J. O'Neil, l. Org. Chern. 30, 2082 (1965); E. E. Schweizer, l. Arn. Chern. Soc. 86,2744 (1964).

14. J. Adams, L. Hoffman, Jr., and B. M. Trost, l. Org. Chern. 35, 1600 (1970). 15a. G. Wittig and H.-D. Frommeld, Chern. Ber. 97, 3548 (1964).

b. R. J. Sundberg, P. A. Bukowick, and F. O. Holcombe, l. Org. Chern. 32, 2938 (1967). c. D. R. Howton, l. Org. Chern. 10, 277 (1945). d. R. N. McDonald and T. W. Campbell, l. Org. Chern. 24, 1969 (1959). e. Y. Chan and W. W. Epstein, Org. Synth. 53, 48 (1973).

16. M. P. Cooke, Jr., and R. Goswami, l. Arn. Chern. Soc. 95, 7891 (1973). 17. P. M. McCurry, Jr., and R. K. Singh, 1. Org. Chern. 39, 2316 (1974). 18. K. D. Sears, R. L. Casebier, H. L. Hergert, G. H. Stout, and L. E. McCandlish, l. Org. Chern. 39,

3244 (1974). 19a. R. M. Coates and J. E. Shaw, 1. Arn. Chern. Soc. 92, 5657 (1970).

b. K. Mitsuhashi and S. Shiotoni, Chern. Pharrn. Bull. 18, 75 (1970). 20. G. BUchi and H. WUest, He/v. Chirn. Acta 54, 1767 (1971).

Chapter 3

2. G. V. Smith and R. L. Burwell, Jr., 1. Arn. Chern. Soc. 84, 925 (1962). 3a. H. W. Thompson, l. Org. Chern. 36, 2577 (1971).

b. E. Piers, W. de Waal, and R. W. Britton, l. Arn. Chern. Soc. 93, 5113 (1971). 4. G. V. Smith and R. L. Burwell, Jr., l. Arn. Chern. Soc, 84,925 (1962). 5. D. J. Pasto and J. A. Gontarz, 1. Arn. Chern. Soc. 93, 6902 (1971). 6. J. Fried and .E. F. Sabo, 1. Arn. Chern. Soc. 79, 1130 (1957). 7a. H. C. Brown,M.M. Rogic, H. Nambu, and M. W. Rathke,1.Aht. Chern. Soc. 91, 2147 (1969);H. C.

Brown, H. Nambu, and M. M. Rogic, l. Arn. Chern. Soc. 91, 6852 (1969). b. H. C. Brown and R. A. Coleman, l. Arn. Chern. Soc. 91, 4606 (1969).

c. H. C. Brown and G. W. Kabalka, 1. Arn. Chern. Soc. 92, 714 (1970). d. G. Zweifel, R. P. Fisher, J. T. Snow, and C. C. Whitney, 1. Arn. Chern. Soc. 93, 6309 (1971). e. H. C. Brown and M. W. Rathke, 1. Arn. Chern. Soc. 89, 2738 (1967). f. H. C. Brown and M. M. Rogic, 1. Arn. Chern. Soc. 91,2146 (1969).

8. A. Pelter, M. G. Hutchings, and K. Smith, Chern. Cornrnun., 1048 (1971); H. C. Brown, B. A. Carlson, and R. H. Prager, 1. Arn. Chern. Soc. 93, 2070 (1971).

9. D. J. Pasto and C. C. Cumbo, 1. Arn. Chern. Soc. 86, 4343 (1964). 10. D. J. Pasto and J. A. Gontarz, 1. Arn. Chern. Soc. 93,6902 (1971). 11. H. C. Brown, P. J. Geoghegan, Jr., G. J. Lynch, and J. T. Kurek, 1. Org. Chern. 37,1941 (1972). 12a. E. Kloster-Jensen, E. Kovats, A. Eschenmoser, and E. Heilbronner, He/v. Chirn. Acta 39, 1051

(1956). b. P. N. Rao, 1. Org. Chern. 36,2426 (1971). c. W. I. Fanta and W. F. Erman, 1. Org. Chern. 33, 1656 (1968). d. W. E. Billups, J. H. Cross, and C. V. Smith, 1. Arn. Chern. Soc. 95, 3438 (1973).

13a. J. Meinwald and J. K. Crandall, 1. Arn. Chern. Soc. 88,1292 (1966). b. H. Stetter and J. Glirtner, Chern. Ber. 99, 925 (1966). c. W. Barbieri, A. Consonni, and R. Sciaky, 1. Org. Chern. 33, 3544 (1968). d. P. E. Peterson and J. E. Duddey, 1. Arn. Chern. Soc. 85,2865 (1963). e. L. A. Paquette and G. R. Krow, Tetrahedron Lett., 2139 (1968).

l4a. K. Izawa, T. Okuyama, T. Sakagami, and T. Fueno, 1. Arn. Chern. Soc. 95, 6752 (1973). b. G. Stork and R. Borch, 1. Arn. Chern. Soc. 86, 935 (1964).

15. R. L. Burwell, Jr., Acc. Chern. Res. 2, 289 (1969). 16. J. Hooz and D. M. Gunn, 1. Arn. Chern. Soc. 91,6195 (1969). 17a. G. Zweifel, J. T. Snow, and C. C. Whitney, 1. Arn. Chern. Soc. 90, 7139 (1968).

b. H. C. Brown, M. M. Rogic, M. W. Rathke, and G. W. Kabalka, 1. Arn. Chern. Soc. 89,5709 (1967). c. A. Hassner, R. P. Hoblitt, C. Heathcock, J. E. Kropp, and M. Lorber, 1. Arn. Chern. Soc. 92,1326

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18. D. G. Garratt, A. Modro, K. Oyama, G. H. Schmid, T. T. Tidwell, and K. Yates, 1. Arn. Chern. Soc. 96,5295 (1974).

Chapter 4

lb. W. Parker, R. Ramage, and R. A. Raphael, 1. Chern. Soc., 1558 (1962). d. S. Yamamura, M. Toda, and Y. Hirata, Org. Synth. 53, 86 (1973).

2. D. C. Wigfield and D. J. Phelps, 1. Arn. Chern. Soc. 96,543 (1974). 3a. E. J. Corey, T. K. Schaaf, W. Huber, U. Koelliker, and N. M. Weinshenker, 1. Arn. Chern. Soc. 92,

397 (1970). b. E. J. Corey and R. Noyori, Tetrahedron Lett., 311 (1970). c. R. F. Borch, Org. Synth. 52, 124 (1972). d. D. Seyferth and V. A. Mai, 1. Arn. Chern. Soc. 92, 7412 (1970).

4a. J. E. Siggins, A. A. Larsen, J. H. Ackerman, and C. D. Carabateas, Org. Synth. 53, 52 (1973). b. W. Sucrow, Tetrahedron Lett., 4725 (1970). c. P. A. Grieco, 1. Arn. Chern. Soc. 91, 5660 (1969). d. R. S. Lenox and J. A. Katzenellenbogen, 1. Arn. Chern. Soc. 95,957 (1973). e. V. BaZant, M. Capka, M. Cerny, C. Chvalovsky, K. Kochloefi, M. Kraus, and J. Malek, Tetrahedron

Lett., 3303 (1968). f. L. I. Zakharkin and I. M. Khorlina, Tetrahedron Lett., 619 (1962).

5a. S. Krishnamurthy, R. M. Schubert, and H. C. Brown, 1. Arn. Chern. Soc. 95, 8486 (1973). b. C. W. Jefford, D. Kirkpatrick, and F. Delay, 1. Arn. Chern. Soc. 94, 8905 (1972). c. J. San Filippo, Jr., and G. M. Anderson, 1. Org. Chern. 39, 473 (1974).

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18a. E. J. Corey, J. A. Katzenellenbogen, N. W. Gilman, S. A. Roman, and B. W. Erickson, 1. Am. Chem. Soc. 90,5618 (1968).

b. A. W. Burgstahler and L. R. Worden, 1. Am. Chem. Soc. 83, 2587 (1961).

Chapter 5

la. K. Hafner and H. Kaiser, Org. Synth. V, 1088 (1973). b. D. Seyferth, J. Fogel, and J. K. Heeren, 1. Am. Chem. Soc. 88,2207 (1966). C. R. A. Benkeser and F. J. Riel, 1. Am. Chem. Soc. 73,3472 (1951). d. J. E. Baldwin, G. A. Hoffe, and O. W. Lever, Jr., 1. Am. Chem. Soc. 96,7125 (1974). e. G. H. Posner, C. E. Whitten, and J. J. Sterling, 1. Am. Chem. Soc. 95,7788 (1973).

f. D. J. Peterson, 1. Am. Chern. Soc. 93, 4027 (1971). g. R. S. Bly and R. L. Veazey, 1. Am. Chern. Soc. 91, 4221 (1969).

2a. B. M. Graybill and D. A. Shirley, 1. Org. Chern. 31, 1221 (1966). b. S. Akiyama and J. Hooz, Tetrahedron Lett., 4115 (1973). c. C. D. Broaddus, 1. Org. Chern. 35, 10 (1970). d. D. A. Shirley and P. A. Roussel, 1. Am. Chern. Soc. 75,375 (1953). e. K. P. Klein and C. R. Hauser, 1. Org. Chern. 32, 1479 (1967). f. D. J. Peterson and H. R. Hays, 1. Org. Chern. 30, 1939 (1965).

3a. M. P. Dreyfuss, 1. Org. Chern. 28, 3269 (1963). b. P. J. Pearce, D. H. Richards, and N. F. Scilly, Org. Synth. 52, 19 (1972). c. U. Schollkopf, H. Kiippers, H.-J. Traenckner, and W. Pitteroff, lustus Liebigs Ann. Chern. 704, 120

(1967). d. J. V. Hay and T. M. Harris, Org. Synth. 53,56 (1973). e. E. L. Eliel, R. O. Hutchins, and M. Knoeber, Org. Synth. 50, 38 (1970). f. J. C. H. Hwa and H. Sims, Org. Synth. V, 608 (1973).

4a. C. R. Johnson, R. W. Herr, and D. M. Wieland, 1. Org. Chern. 38, 4263 (1973). b. E. J. Corey and P. L. Fuchs, 1. Am. Chern. Soc. 94, 4014 (1972). c. W. G. Dauben and A. J. Kielbania, Jr., 1. Am. Chern. Soc. 93, 7345 (1971). d. c. R. Johnson and G. A. Dutra, 1. Am. Chern. Soc. 95, 7777 (1973). e. R. A. J. Smith and T. A. Spencer, 1. Org. Chern. 35, 3220 (1970). f. H. O. House and M. J. Umen, 1. Org. Chern. 38, 3893 (1973).

5. P. S. Skell and G. P. Bean, 1. Am. Chern. Soc. 84, 4660 (1962). 6. E. c. Ashby, J. Laemmle, and H. M. Neumann, 1. Am. Chern. Soc. 93, 4601 (1971). 7. M. Newcomb and W. T. Ford, 1. Am. Chern. Soc. 95, 7186 (1973). 8. R. W. Herr and C. R. Johnson, 1. Am. Chern. Soc. 92, 4979 (1970). 9. G. Zon and L. A. Paquette, 1. Am. Chern. Soc. 96,215 (1974).

10. P. G. Gassman, G. R. Meyer, andF.J. Williams,l. Am. Chern. Soc. 94, 7741 (1972);P. G. Gassman and F. J. Williams, 1. Am. Chern. Soc. 94,7733 (1972).

11. R. K. Russell, R. E. Wingard, Jr., and L. A. Paquette, 1. Am. Chern. Soc. 96, 7483 (1974). 12a. E. O. Fischer, K. Ofele, H. Essler, W. Frohlich,J. P. Mortensen, and W. Semmlinger, Chern. Ber. 91,

2763 (1958). b. R. Pettit, 1. Am. Chern. Soc. 81, 1266 (1959). c. M. Dubeck and A. H. Filbey, 1. Am. Chern. Soc. 83, 1257 (1961). d. M. P. Cooke, Jr., 1. Am. Chern. Soc. 92, 6080 (1970). e. C. H. Wei and L. F. Dahl, 1. Am. Chern. Soc. 88, 1821 (1966).

13a. M. F. Semmelhack and H. T. Hall, 1. Am. Chern. Soc. 96, 7091 (1974). b. M. L. H. Green and P. L. I. Nagy, 1. Organornetal. Chern. 1, 58 (1963).

14a. E. J. Corey and R. L. Carney, 1. Am. Chern. Soc. 93,7318 (1971). b. W. G. Dauben, G. Ahlgren, T. J. Leitereg, W. C. Schwarzel, and M. Yoshioko, 1. Am. Chern. Soc.

94,8593 (1972). c. S. W. Pelletier and S. Prabhakar, 1. Am. Chern. Soc. 90, 5318 (1968). d. E. J. Corey, D. E. Cane, and L. Libit, 1. Am. Chern. Soc. 93, 7016 (1971). e. R. D. Clark and C. H. Heathcock, Tetrahedron Lett., 1713 (1974); W. G. Dauben,J. W. McFarland,

and J. B. Rogan, 1. Org. Chern. 26, 297 (1961). 15a. E. J. Corey, C. U. Kim, R. H. K. Chen, and M. Takeda, 1. Am. Chern. Soc. 94, 4395 (1972).

b. J. A. Marshall, W. F. Huffman, and J. A. Ruth, 1. Am. Chern. Soc. 94, 4691 (1972). c. L. Watts, J. D. Fitzpatrick, and R. Pettit, 1. Am. Chern. Soc. 88, 623 (1966). d. H. A. Whaley, 1. Am. Chern. Soc. 93, 3767 (1971). e. J. A. Marshall, W. F. Huffman, and J. A. Ruth, 1. Am. Chern. Soc. 94, 4691 (1972). f. M. F. Semmelhack and P. M. Helquist, Org. Synth. 52, 115 (1972). g. L. S. Hegedus and R. K. Stiverson, 1. Am. Chern. Soc. 96,3250 (1974). h. G. D. Prestwich and J. N. Labovitz, 1. Am. Chern. Soc. 96, 7103 (1974).

Chapter 6

1. J. E. Baldwin and R. K. Pinschmidt, Jr., 1. Am. Chern. Soc. 92,5247 (1970). 2. H. E. Zimmerman, G. L. Grunewald, R. M. Paufier, and M. A. Sherwin, 1. Am. Chern. Soc. 91, 2330

(1969).

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27. L. N. Mander and J. V. Turner, I. Org. Chern. 37, 2915 (1972).

Chapter 7

lb. E. C. Taylor, F. Kienzle, R. L. Robey, and A. McKillop, I. Am. Chern. Soc. 92, 2175 (1970).

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10. P. B. D. de la Mare, O. M. H. el Dusouqui, J. G. Tillett, and M. Zeltner, I. Chem. Soc., 5306 (1964). 11. A. A. Khalaf and R. M. Roberts, I. Org. Chem. 36,1040 (1971). 12a. J. H. Boyer and R. S. Buriks, Org. Synth. V, 1067 (1973).

b. H. P. Schultz, Org. Synth. IV, 364 (1963); F. D. Gunstone and S. H. Tucker, Org. Synth. IV, 160 (1963).

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13a. C. L. Perrin and G. A. Skinner, I. Am. Chem. Soc. 93,3389 (1971). b. R. A. Rossi and J. F. Bunnett, I. Am. Chem. Soc. 94, 683 (1972). C. M. Jones, Jr., and R. H. Levin, 1. Am. Chem. Soc. 91, 6411 (1969).

15a. G. H. Cleland, Org. Synth. 51, 1 (1971). b. G. Smolinsky, 1. Am. Chem. Soc. 82, 4717 (1960). C. J. T. Koo, Org. Synth. V, 550 (1973). d. A. B. Galun and A. Kalir, Org. Synth. 48, 27 (1968).

16a. R. E. Ireland, C. A. Lipinski, C. J. Kowalski, J. W. Tilley, and D. M. Walba, 1. Am. Chem. Soc. 96, 3333 (1974).

b. J. J. Korst, J. D. Johnston, K. Butler, E. J. Bianco, L. H. Conover, and R. B. Woodward, 1. Am. Chem. Soc. 90, 439 (1968).

Chapter 8

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7. P. S. Skell and R. R. Engel, I. Am. Chem. Soc. 88,3749 (1966). 8. P.~. Barieli, G. Berti, B. Macchia, and L. Monti, I. Chem. Soc. C, 1168 (1970). 9. H. O. House and G. A. Frank, 1. Org. Chem. 30, 2948 (1965).

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17. E. W. Warnhoff, C. M. Wong, and W. T. Tai, J. Am. Chem. Soc. 90, 514 (1968).

Chapter 9

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10. E. J. Corey, N. W. Gilman, and B. E. Ganem, 1. Am. Chem. Soc. 90, 5616 (1968). 11. W. S. Trahanovsky, J. R. Gilmore, and P. C. Heaton, 1. arg. Chem. 38, 760 (1973). 12a. J. A. Marshall and R. A. Ruden, 1. arg. Chem. 36, 594 (1971).

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13a. W. S. Johnson, T. Li, C. A. Harbert, W. R. Bartlett, T. R. Herrin, B. Staskun, and D. H. Rich, 1. Am. Chem. Soc. 92, 4461 (1970); W. S. Johnson, M. F. Semmelhack, M. U. S. Sultanbawa, and L. A. Dolak,l. Am. Chem. Soc. 90, 2994 (1968).

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Chapter 10

1a. D. M. Simonovic, A. S. Rao, and S. C. Bhattacharyya, Tetrahedron 19, 1061 (1963). b. R. E. Ireland and L. N. Mander, 1. argo Chem. 32, 689 (1967). c. G. Biichi, W. D. MacLeod, Jr., and J. Padilla 0., 1. Am. Chem. Soc. 86, 4438 (1964). d. P. Doyle, I. R. Maclean, W. Parker, and R. A. Raphael, Proc. Chem. Soc., 239 (1963). e. J. C. Sheehan and K. R. Henery-Logan, 1. Am. Chem. Soc. 84, 2983 (1962). f. E. J. Corey, M. Ohno, R. B. Mitra, and P. A. Vatakencherry, 1. Am. Chem. Soc. 86, 478 (1964).

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9a. Z. G. Hajos and D. R. Parrish, 1. Org. Chern. 39, 1615 (1974). b. L. Hub and H. S. Mosher, 1. Org. Chern. 35, 3691 (1970). C. S. Musierowicz, A. Wroblewski, and H. Krawczyk, Tetrahedron Lett., 437 (1975).

lOa. S. Ohki and T. Nagasaka, Chern. Pharrn. Bull. 19, 545 (1967). b. A. Guyer, A. Bieler, and E. Pedrazzetti, Helv. Chirn. Acta 39,423 (1956). C. S. F. Thames and H. C. Odom, Jr., 1. Heterocycl. Chern. 3, 490 (1966). d. H. C. Beyerman and G. J. Heiszwolf, Recl. Trav. Chirn. Pays-Bas 84,203 (1965). e. S. W. Pelletier, R. L. Chappell, and S. Prabhakar, 1. Am. Chern. Soc. 90,2889 (1968); S. W. Pelletier

and S. Prabhakar, 1. Am. Chern. Soc. 90, 5318 (1968). f. P. Doyle, I. R. MacLean, W. Parker, and R. A. Raphael, Proc. Chern. Soc., 239 (1963). g. M. Kato, H. Kosugi, and A. Yoshikoshi, Chern. Cornrnun., 185 (1970).

11. A. I. Meyers and E. W. Collington, 1. Am. Chern. Soc. 92, 6676 (1970). 12a. I. Fleming, Selected Organic Syntheses, Wiley, London, 1973, pp. 3-6; J. E. McMurry and J. Melton,

1. Am. Chern. Soc. 93,5309 (1971). b. R. M. Coates and J. E. Shaw, 1. Am. Chern. Soc. 92,5657 (1970). C. W. S. Johnson, T. J. Brocksom, P. Loew, D. H. Rich, L. Werthemann, R. A. Arnold, T. Li, and D. J.

Faulkner, 1. Am. Chern. Soc. 92, 4463 (1970); E. E. van Tamelen and J. P. McCormick, 1. Am. Chern. Soc. 92,737 (1970); S. Tanaka, H. Yamamoto, H. Nozaki, K. B. Sharpless, R. C. Michaelson, and J. D. Cutting, 1. Am. Chern. Soc. 96, 5254 (1974); K. Imai, S. Marumo, and K. Mori, 1. Am. Chern. Soc. 96,5925 (1974); D. J. Faulkner and M. R. Petersen, 1. Am. Chern. Soc. 95,553 (1973); J. A. Findlay and W. D. MacKay, Chern. Cornrnun., 733 (1969); H. Schulz and I. Sprung, Angew. Chern. Int. Ed. Eng/. 8, 271 (1969); K. Mori, B. Stalla-Bourdillon, M. Ohki, M. Matsui, and W. S. Bowers, Tetrahedron 25,1667 (1969); W. S. Johnson, T. Li, D. J. Faulkner, and S. F. Campbell, 1. Am. Chern. Soc. 90, 6225 (1968); R. Zurfliih, E. N. Wall, J. B. Siddall, and A. Edwards, 1. Am. Chern. Soc. 90, 6224 (1968); E. J. Corey, J. A. Katzenellenbogen, N. W. Gilman, S. A. Roman, and B. W. Erickson, 1. Am. Chern. Soc. 90, 5618 (1968); E. J. Corey, H. Yamamoto, D. K. Herron, and K. Achiwa, 1. Am. Chern. Soc. 92, 6635 (1970); K. H. Dahm, B. M. Trost, and H. Roller, 1. Am. Chern. Soc. 89, 5292 (1967); P. Loew and W. S. Johnson, 1. Am. Chern. Soc. 93, 3765 (1971).

d. J. H. Babler, D. O. Olsen, and W. H. Arnold, 1. Org. Chem. 39,1656 (1974); R. J. Crawford, W. F. Erman, and C. D. Broaddus, 1. Am. Chem. Soc. 94, 4298 (1972).

e. E. J. Corey and R. D. Balanson, 1. Am. Chem. Soc. 96, 6516 (1974). f. J. L. Herrmann, M. H. Berger, and R. H. Schlessinger, 1. Am. Chem. Soc. 95, 7923 (1973). g. R. F. Romanet and R. H. Schlessinger, 1. Am. Chem. Soc. 96, 3701 (1974); R. A. LeMahieu, M.

Carson, and R. W. Kierstead, 1. Org. Chem. 33, 3660 (1968); G. Biichi, D. Minster, and J. C. F. Young, 1. Am. Chem. Soc. 93, 4319 (1971).

h. E. J. Corey, M. Ohno, R. B. Mitra, and P. A. Vatakencherry, 1. Am. Chem. Soc. 86, 478 (1964). 13a. H. M. Walborsky, T. Sugita, M. Ohno, and T. Inouye, 1. Am. Chem. Soc. 82, 5255 (1960).

b. H. M. Walborsky, L. Barash, and T. C. Davis, 1. Org. Chem. 26, 4778 (1961); Tetrahedron 19, 2333 (1963).

C. W. S. Johnson, C. A. Harbert, and R. D. Stipanovic, 1. Am. Chem. Soc. 90, 5279 (1968). d. M. Mousseron, M. Mousseron, J. Neyrolles, and Y. Beziat, Bull. Soc. Chim. Fr., 1483 (1963); Y.

Beziat and M. Mousseron-Canet, Bull. Soc. Chim. Fr., 1187 (1968).

Chapter 11

4. B. W. Erickson and R. B. Merrifield, 1. Am. Chem. Soc. 95, 3757 (1973). 8a. P. Sieber and B. Iselin, Helv. Chim. Acta 51,614 (1968). b. M. Smith, D. H. Rammler, 1. H. Goldberg, and H. G. Khorana,J. Am. Chem. Soc. 84, 430 (1962). C. P. G. Pietta, P. Cavallo, and G. R. Marshall, 1. Org. Chem. 36, 3966 (1971).

10. S.-S. Wang and R. B. Merrifield, 1. Am. Chem. Soc. 91, 6488 (1969); S.-S. Wang, 1. Am. Chem. Soc. 95, 1328 (1973).

11. B. F. Gisin and R. B. Merrifield, 1. Am. Chem. Soc. 94, 3102 (1972). 13. S. A. Narang, O. S. Bhanot, J. Goodchild, R. H. Wightman, and S. K. Dheer, 1. Am. Chem. Soc. 94,

6183 (1972). 14. E. Ohtsuka, M. Ubasawa, and M. Ikehara,l. Am. Chem. Soc. 92,5507 (1970). 15. J. D. Glass, I. L. Schwartz, and R. Walter, 1. Am. Chem. Soc. 94, 6209 (1972). 16. H. K. Hall, Jr., and M. J. Steuk, 1. Polym. Sci. Polym. Chem. Ed. 11, 1035 (1973); H. K. Hall, Jr.,

L. J. Carr, R. Kellman, and F. De Blauwe, 1. Am. Chem. Soc. 96, 7265 (1974). 17a. T. Saegusa, Y. Kimura, K. Sano, and S. Kobayashi, Macromolecules 7, 546 (1974).

b. P. M. Hergenrother, Macromolecules 7, 575 (1974). C. K. Teranishi, M. Iida, T. Araki, S. Yamashita, and H. Tani, Macromolecules 7, 421 (1974). d. J. K. Stille and G. K. Noren, Macromolecules 5, 49 (1972).

18. K. E. Pfitzner and J. G. Moffatt, 1. Am. Chem. Soc. 87, 5661 (1965).

507

REFERENCES FOR

PROBLEMS

Subject Index

acetals, protecting groups for alcohols 408, 409 aldehydes 416, 417 diols 410

acetate esters, pyrolysis of 245 acetonides, as derivatives of diols 410, 413 acidity

of carbon acids (table) 3 of phosphonium salts 54

acrylonitrile conjugate addition to 25 polymerization of 461

acylation of dimethyl sulfoxide 52 of esters 47-51 Friedel-Crafts 267,268,270,271

acylium ions, in Friedel-Crafts reactions 261 acyloin condensation 145

intramolecular 148 1,2- and 1,4-addition to dienes 94 alcohols

acylation by N- acylimidazoles 411 of hindered 411

optically active, by asymmetric synthesis 424, 425 oxidation of 351-359,395,396

by chromium(VO 351-355 by dimethyl sulfoxide 356-358 by Oppenauer method 358, 359

protecting groups for 408-414 synthesis

by hydration of alkenes 85-87 by hydroboration -oxidation 100-105 from organometallic reagents 171-175 by oxymercuration 87-89 by reduction of carbonyl compounds 129,

130, 134-139 by reduction of epoxides 139

alcohols (continued) tertiary, from organoboranes by carbonylation

106,107 unsaturated, synthesis

from epoxides 369, 370 by singlet-oxygen oxidation of alkenes 390,

391 aldehydes

alkylation of 19 dithiane derivatives of 419,420 oxidation of 381-387 photochemical addition to alkenes 226 reactions with

aromatic rings 269 organometallic reagents 171-175

synthesis from a-alkoxyalkylphosphoranes 423 from Grignard reagents and triethyl ortho­

formate 172, 173 from ole fins using chromyl chloride 360, 361 by oxidation

of alcohols 351-359 of terminal alkenes 360

by ozonolysis 372-377 by reduction

of acylaziridines and imidazolides 132 of carboxylic acid chlorides 132 of esters 13 3 of nitriles 132, 133

by Vilsmeier-Haack reaction 270, 271 aldol condensation 33-42

as side reaction in alkylation of ketones 10 alkenes

asymmetric hydroboration of 425 complexes with transition metals 194 epoxidation of 362-365 formation in carbene rearrangements 316-318 halogenation 90-95

509

510

SUBJECT INDEX

alkenes (continued) hydration 85-87 hydroboration 100-112 hydrogenation 73-81 hydroxylation 359-361 oxidation of 359-363

allylic 372, 387-393 by chromium (VI) 372, 387, 388 by chromyl chloride 360,361 by osmium tetroxide 360 by ozone 373-377 by permanganate ion 359, 360, 371, 372 by peroxidic reagents 362-364

oxymercuration 87-90 photochemical cycioaddition reactions 222-

226 polymerization 461467 reactions with

carbenes 303, 310-315 hydrogen halides 81-85 ozone 373-377 selenyl halides 392 trifluoroacetic acid 86

reactivity toward 1,3-dipolar reagents 217 as reagents in Friedel-Crafts reactions 265 reduction with diimide 80, 81 synthesis

by acetate pyrolysis 245 by amine oxide pyrolysis 242-244 by hydroboration of alkynes 118 from ketones via tosylhydrazones 318, 319 via a-trimethylsilyl alkyllithium reagents 59 by Wittig reactions 53-58

alkylation of aldehydes 19 of dian ions 12, 13 of enamines 23 of enolates 8-19 of esters 20 Friedel-Crafts 261-272 of hydroxymethylene ketones 52 of imino magnesium halides 24 of nitriles 20 of nitro compounds 20 at oxygen

of enolates 15-19 of phenolate anions 18 of nitronate ions 20

of a,p-unsaturated ketones 18, 19 alkyl halides (see halides, alkyl) alkyllithium compounds (see lithium, organo-,

reagents) alkynes

additions of dialkylaluminum hydrides to 119 2+2 cyc1oaddition reactions of 225 electrophilic additions to 112-117 hydrogenation of 11 7 reduction of 116

alkynylmagnesium halides, preparation of 165 allenes

cycioaddition reactions of 220, 221 electrophilic addition to 112-117 formation from cyclopropylidenes 318 protonation of 112

1T-allyl complexes of nickel 187 , 189 allyl ethers, as alcohol-protecting group 409 allyl halides (see halides, allyl) allylic alcohols (see alcohols, unsaturated) aluminum, vinyl derivatives of as synthetic inter-

mediates 119-121 amides

conversion to amines by Hofmann rearrange­ment 331

reduction by diborane 134 by lithium aluminum hydride 130, 131

. synthesis from alkenes by oxymercuration 90 by Beckmann rearrangement 328, 329 from ketones by reaction with hydrazoic

acid 333 amine oxides, pyrolysis of 242 amines

hydroxy, rearrangement of 337-339 protective groups for 414,415 synthesis

by alkylation of phthalimide 415 from carboxylic acid derivatives 330-333 from organoboranes 105, 106 by reduction of

amides 130, 131 imines 13 3, 134 nitro compounds 146 oximes 146

amino acids amino-protecting groups for 474, 475 carboxyl-protecting groups for 475 peptide and protein synthesis from 472482 sequence in bovine insulin 473

anhydrides (see carboxylic acid anhydrides) anilines

conversion to aryldiazonium ions 275, 276 as precursors of benzynes 286

anionic polymerization 465, 466, 469 anthracene, reactivity of 292-294 antithetic transform 449 aromatic compounds

addition reactions with carbenes 313 as diene components in Diels-Alder reac-

tions 210, 211 dissolving-metal reduction of 147, 151 reactions with nitrenes 321, 322 side-chain oxidations 393-395

asymmetric synthesis 423429 in Claisen rearrangements 230 in homogeneous hydrogenation 80

asymmetric synthesis (continued)

in reduction of ketones with Grignard re­agents 173

atactic polymers 467 ate complexes 120, 121

of copper 182-186 azides

acyl, Curtius rearrangement of 329-331 acyl, in synthesis of peptides 478, 479 alkyl, in synthesis of secondary amines from

organoboranes 106 aryl, from diazonium salts 280 as precursors of nitrenes 320-322

aziridines acyl, in aldehyde synthesis 132 cyc1oreversion on reaction with difluoroamine

235,236 ring-opening of, in cyc1oadditions 217,218 synthesis by nitrene addition reactions 321 in synthesis of oxazoline derivatives 417,418

azo compounds, thermal elimination of nitrogen from 237-242

azomethines (see imines)

Baeyer-Villiger oxidation 383-385,445,446 basic catalysts, strength of 3 Beckmann rearrangement 328, 329

fragmentation in 334-336 benzyl ethers

as alcohol-protecting groups 409, 413 hydrogenolysis of 76

benzyne 282-288 bonding in 282 cycIoaddition reactions of 286-288 generation of 282-286 reviews 294

betaine intermediate, in Wittig reaction 55 bicyclic rings, synthesis of

from enamines 27 by intramolecular reactions of diazoketones

340 via Mannich reaction 46

biogenetic-type synthesis polyolefm cyclizations 340-343 of tropinone 46

Birch reduction 151, 152 block copolymers 469 bond-switching reactions 191-193 9-borabicyc1ononane (9-BBN)

as selective hydroboration reagent 102 in synthesis of aldehydes 107, 108

borane-dimethyl sulfide adduct 101 boranes 100-112

fragmentation reactions of 336 in preparation of stereoselective reducing

agents 428,429 stereoselective reactions of 425, 426 substituted, additions to alkenes 102

Bouvault-Blanc reduction 145 bromides, alkyl (see also halides)

from alkenes by addition of hydrogen bromide 81-85

from organoboranes 106 bromides, vinyl, synthesis from alkynes via hydro­

boration 118, 119 bromination

of alkenes 90-95 of alkynes 116 of aromatic compounds 261 of ketones 98-100 stereochemistry of 91, 92

a-bromoacrolein, as synthetic equivalent of allene oxide 438

N-bromoamides, in Hofmann rearrangement 331 bromohydrins, synthesis of 93,94 N bromosuccinimide

in synthesis of bromohydrins 93, 94 in synthesis of a-bromoketones 99

bulk polymerization 462 t-butoxycarbonyl, as amino-protecting group

414,474 t-butyldimethylsilyl ethers, as alcohol-protecting

group 410

cadmium, alkyl derivatives 165,180 Cannizzaro reaction 141, 142 carbanions

alkylation of 8-12,170,171 basicity of 1-3 resonance stabilization of 2

carbenes 301-320 a-acyl, equilibrium with oxirenes 323 addition to benzene 313 in epoxide ring-()pening 369 generation 304-311, 318 insertion reactions 313-316 reactivity 303, 304 rearrangements 316-320 reviews 343 stereochemistry of addition, singlet versus

triplet 303, 311, 312 structure and bonding in 302-304

carbobenzyloxy group, as protecting group 77, 414,474

carbonium ions in addition of hydrogen halides to alkenes 84,85 in addition of trifluoroacetic acid to alkenes 86 in chlorination of alkenes 92 cyclization of 340-343 in electrophilic addition to allenes 112 in epoxide ring-()pening 368-370 in fragmentation reactions 333-336 in Friedel-Crafts reactions 261 in lead tetraacetate decarboxylation reactions

380 in Meerwein arylation reactions 291

511 SUBJECf

INDEX

512 SUBJECT INDEX

carbonium ions (continued) rearrangements

in cationic polymerization 464 in Friedel-Crafts alkylation 262-264 in pinacol-pinacolone rearrangements 336-

338 in reactions of epoxides 368-370

reduction by silanes 143 carbon monoxide, reaction with organoboranes

106-108 carbonylation

of aromatic rings 269, 272 of organoboranes 106-108

carboxylic acid anhydrides in Friedel-Crafts acylation 267 mixed, as acylating agents 411, 476 in peptide synthesis 476

carboxylic acid chlorides in Friedel-Crafts acylation 267 reaction with

organocadmium reagents 180, 181 organocuprate reagents 185, 186 tri-n-butyltin hydride 144, 145

carboxylic acids esterification by diazoalkanes 418 homologation via Wolff rearrangement 322,

323 oxidative decarboxylation by lead tetraacetate

379-381 protecting groups for 417,475 synthesis

from Grignard reagents by carbonation 173-175

by hypo halite oxidation of methyl ketones 387

unsaturated, by Knoevenagel reaction 43 unsaturated, via organoaluminum reagents

119,120 caryophyllene, synthesis 440 catalysts

for Friedel-Crafts reactions 264, 265 homogeneous, for hydrogenation 79, 80

cationic polymerization 462-465 chain-addition polymerization 460-467 chlorides (see also halides)

alkyl, from alkenes by addition of hydrogen chloride 81-85

benzyl, by aromatic chloromethylation 268 chlorination

of alkenes 90-95 of alkynes 116 of aromatic compounds 260-263 of ketones 99

a-ch10roacrylonitrile, as ketene equivalent in Diels-Alder reaction 421

a-ch10roketones, from reaction of alkenes with chromyl chloride 361

chloromethylation, of aromatic compounds 268

m-chloroperoxybenzoic acid in Baeyer-Villiger oxidation 384, 385 epoxidation of alkenes by 362-364 for stereo selective oxidation 438-439

N-chlorosuccinimide 357 chromium trioxide

in allylic oxidation 387, 388 complex with pyridine as oxidant 352-354 as oxidant 351-354 oxidation of ketones by 381, 382 oxidation of saturated hydrocarbons by 393,

394 reaction with alkenes 372

chromyl chloride, reaction~ with alkenes, 360, 361

Chugaev reaction 246, 247 Claisen condensation 47-49

as side reaction in alkylation of ester enolates 10 Claisen rearrangement 227-231

of allyl phenyl ethers 230, 231 of allyl vinyl ethers 227, 228 stereochemistry 230, 231 of trimethylsilyl enol ethers of allylic esters

229 Claisen-Schmidt condensation 40-42 Oemmensen reduction 148, 149 Collins reagent 353-355 computer-assisted organic synthesis 449 condensation polymerization (see step-growth

polymerization) condensation reactions

acyloin 145 aldol 33-42 Claisen 10,47-49 Claisen-Schmidt 40-42 Dieckmann 48-50 Knoevenagel42-44

conjugate addition alkylation by 24-27 of cuprate reagents 184-186 of Grignard reagents 176 of sulfur ylides to unsaturated ketones 60-63

convergent synthesis 430 coordination polymerization 466, 467 Cope rearrangement 231-234 copolymerization 462, 465, 469 copper salts, as catalysts

for decomposition of diazo compounds 307 in reactions of aryl diazonium salts 276, 277 in reactions of aryl halides 288 in reaction of Grignard reagents with un­

saturated compounds 176 as reagents for aromatic iodination 261

Cram's rule 425 cuprate reagents

oxidative dimerization 190 preparation 182, 183 reactions 183-187

Curtius rearrangement 322, 329-332 cyanides (see nitriles) cyanoethyl, as protecting group in oligonucleo­

tide synthesis 488 cyanohydrins

as acyl anion equivalents 419-421 formation of 339 reduction of 338

cycloaddition reactions 205-226 of benzyne 286-288 Diels-Alder reaction 206-212 1,3-dipolar 212-219 photochemical 222-226 of polycyclic aromatic compounds 293

cyclobutadieneiron tricarbonyl 195, 196 cyclobutanes, synthesis

by cycloaddition reactions 220, 221 by photocyclization of dienes 223, 224

cyclobutanones, synthesis 220 cyclopropanes

dihalo-, formation from alkenes and dihalocar­benes 303, 311-313

formation in intramolecular insertion reactions of carbenes 316

photochemical cleavage 309 synthesis 216, 312

by thermolysis of pyrazolines 242 from o<,j3-unsaturated carbonyl compounds

and sulfur ylides 60,61-63 cyclopropanones

dipolar form in cycloaddition reactions 218, 219

as intermediates in Favorskii reaction 324-326 cyclopropenes, formation from vinylcarbenes

319 cycloreversion reactions 234-242

Darzens reaction 63, 64 deamination

of aziridines 235, 236 of 3-pyrrolines 235

decarbonylation, of unsaturated cyclic ketones 236

dianions, generation and alkylation 12, 13,52 diazirines, as carbene precursors 308 diazo compounds, as source of carbenes 305-307 diazoketones

from carboxylic acid chlorides and diazometh­ane 306

conversion to ketenes 322-324 reaction with organoboranes 112

diazomethane reaction with carboxylic acid chlorides 306 synthesis of 305, 306

diazonium ions, aryl conversion to aryl halides 277-280 replacement of nitrogen by hydrogen 277 as synthetic intermediates 275-280

diborane generation 101 reaction with alkenes 100-103 reaction with epoxides 369 in reduction of carbonyl groups 130, 134

dicyclohexylcarbodiimide, as reagent for coupling of nucleotides 489 in oxidation of alcohols 356, 357 for peptide synthesis 477

Dieckmann condensation 48-50, 440, 441 Diels-Alder reaction 206-212, 236, 437,438

"asymmetric synthesis via acrylate esters 426, 427

of benzyne 286-288 catalysis of 209 o<-chloroacetonitrile as dienophile 420,421 in prostaglandin synthesis 434,444,445 regioselectivity of 208 stereochemistry of 207 in synthesis of fumagillol437, 438

dienes 1,5-, Cope rearrangement of 231-234 1,3-, halogenation of 94 photochemistry of 223, 224 synthesis, from vinyllithium reagents 190

dienophiles, in Diels-Alder reaction 207, 210 diirnide, as reducing agent 80, 81 diisobutylaluminum hydride

in partial reduction of esters and lactones 133 reduction of nitriles by 133 reduction of unsaturated ketones by 138,139

N,N-dimethylacetamide dimethyl acetal, reac-tion with allylic alcohols 228

dimethyloxosulfonium methylide 59 dimethylsulfonium methylide 59 dimethyl sulfoxide

bromohydrin formation in 93 as reagent in oxidation of alcohols 356-358 as solvent in amine oxide pyrolysis 243

dipolar aprotic solvents 13, 14 1,3-dipolar cycloaddition reactions 212-219 dipolar intermediates, in 2+2 cycloaddition reac-

tions 220, 221 1,3-dipolar molecules 212-214 dipolarophiles, in 1,3-dipolar cycloaddition reac­

tions 213 diradical intermediate, in thermolysis of cyclic

azo compounds 240 dissolving-metal reductions 145-152 1,3-dithianes, as acyl anion equivalents 419-421 cis-divinylcyclobutane, Cope rearrangement of 234 cis-divinylcyclopentane, ~ope rearrangement of

234 cis-divinylcyclopropane, Cope rearrangement of

233,234

effective atomic number rule, in transition-metal complexes 196

513 SUBJECT

INDEX

514 SUBJECT INDEX

electrophilic aromatic substitution 257-275 Friedel-Crafts 261-272 halogenation 260-263 metaiation 272-275 nitration 257-260 in polycyclic aromatics 292, 293

elimina tion reactions cr-elimination in epoxide ring-opening 369 O!-elimination route to carbenes 309, 310 thermal 242-247

emulsion polymerization 462 enamines

alkylation of 22-24 in 2+2 cycloaddition reactions 220, 221 preparation of 21, 22 protonation of 22 reaction with 1,3-dipolar reagents 216, 218 reaction with electrophilic alkenes 220, 221 steric effects in 22

enol acetates by acetylation of enolate ions 5 by addition of acetic acid to alkynes 114 epoxidation of 371

enolates acylation of 47-53 alkylation of 1, 8-12 ambident character of 15-19 carbon versus oxygen alkylation of 15-19 generation of

by cleavage of enol trimethylsilyl ethers with methyllithium 7,10

by deprotonation 1-6 by reduction of O!,fj-unsaturated carbonyl

compounds 7 oxidation by molecular oxygen 384-386 solvent effects on reactivity of 12-19 stereochemistry of alkylation 11, 12 structure and stability 3-6 sulfenylation of 99,100 of O!,/3-unsaturated ketones 5

enol ethers of fj-dicarbonyl compounds, reduction by

LiAlH.139 polymerization of 463 preparation by Wittig reaction 58, 423 as reactants in 2+2 cycloaddition reactions

221,222 enolization

of hydroxymethylene ketones 51 of ketones in reactions with Grignard reagents

173 enols, as intermediates in ketone bromination

98,99 episulfones, thermal elimination of SO. from

237 epoxides

as carbene precursors 308 dissolving-metal reduction of 146

epoxides (continued) as intermediates in pinacolic rearrangement

337 photochemical generation of carbenes from

308,309 polymerization of 466 reactions of 365-371

with cuprate reagents 183, 186 with diborane 369 with LiAlH. 139, 366-368

rearrangement to carbonyl compounds 370, 371

reduction by metal hydrides 367,368 ring-opening of 364-371

in initiation of polyolefin cyclization 341-343

synthesis by Darzens reaction 62 by epoxidation of alkenes 362-364 with sulfur ylides 60

esterifica tion of alcohols 411 of amino acids 475 of carboxylic acids 418

esters acyloin condensation of 145 alkylation of 19, 20 allyl

reactions with cuprate reagents 185, 186 synthesis by oxidation of alkenes with sele­

nium dioxide 392 thermal rearrangement of, via trimethylsilyl

enol ethers 229 base-catalyzed condensation with ketones 42 dissolving-metal reductions of 145 enolates of, sulfenylation 99 reaction with Grignard reagents 172 synthesis

from alkenes 86 by Baeyer-Villiger oxidation of ketones

383-386 thermal elimination reactions of 245,246

ethers, synthesis via oxymercuration 89, 90 ethyl orthoacetate, as reagent in Claisen rear­

rangement of allyl alcohols 228-230 ethyl orthoformate, reaction with Grignard re­

agents in synthesis of aldehydes 172-175 N-ethyl-5-phenylisoxazolium sulfonate, as re­

agent for peptide synthesis 477, 478

Favorskii rearrangement 324;327 ferrocene 195-197 fragmentation reactions 333-336

in chromic acid oxidations 353 free-radical substitution

in aromatic systems 288-292 partial rate factors for 289

Friedel-Crafts reaction 261-272 catalysts for 265 intramolecular 265, 267 isomer ratio in 264 rearrangement during 262-264, 266 reviews 294

fluorides (see also halides) aryl, synthesis via diazonium salts 280

fumagillol, synthesis of 437-440

Gabriel amine synthesis 415 glycols

oxidative cleavage of 371-373,377-379 , protection as carbonate esters 414

protection as dioxolanes 410, 411 synthesis

by hydrolysis of epoxides 364-366 by hydroxylation of alkenes 359, 360

Grignard reagents addition to carbonyl compounds 171-179,

424,425 configurational stability 168 coupling reactions catalyzed by Co(Il), Ni(III),

and TI(I) 189 preparation and properties 164-166 reaction with ethyl orthoformate 172 reaction with oxygen and peroxides 176, 177 reduction of ketones by 143, 173 stereochemistry of reaction with ketones 424,

425 unsaturated, structures of 179, 180

halides (see also bromides, chlorides, fluorides, iodides)

alkyl as precursors of carbenes by a-elimination

309,310 reactions with

cuprate reagents 184, 185, 187 Grignard reagents, nickel-catalyzed 189 magnesium 163 organolithium reagents 170, 171, 178 organonickel reagents 187, 188

reduction by dissolving metals 151, 152 metal hydrides 139-141 tri-n-butyltin hydrides 143, 144

synthesis from carboxylic acids with decarboxyla­

tion 380 via hydroboration 106 by hydrogen halide addition to alkenes 81-

85 from organomercury compounds 180

allyl coupling by nickel reagents 188, 189 reaction with phenyllithium 170, 171

halides (continued)

aryl conversion to nitriles 288, 289 copper-catalyzed nucleophilic substitution

288 coupling by bis(l ,5-cyclooctadiene)nickel(0)

188 generation of benzyne from 284 reaction with lithium dimethyl cuprate 184 reactivity toward nucleophilic substitution

281,282,284 substitution via electron-transfer reactions

291,292 synthesis from aryl diazonium ions 277-280 in Ullmann reaction 190, 191

vinyl coupling with bis(1,5-cyclooctadiene)nickel

(0) 189 formation from ate complexes 121 formation from vinylalanes 119

a-haloalkyllithium reagents 309, 310 a-haloesters

in Darzens reaction 63 reaction with organoboranes 11 0, 111 in Reformatsky reaction 181, 182

halogenation of alkenes 90-93 of aromatic compounds 260-263 of dienes 94, 95 stereochemistry 91, 92

halogen-metal exchange 166 stereochemistry of 168

halohydrins, synthesis of 93-94 a-haloketones

base-catalyzed rearrangement of 324-327 as intermediates in hypohalite oxidation of

methyl ketones 387 in Reformatsky reaction 182 synthesis by epoxidation of vinyl halides 371

Hilbert-Johnson procedure for nucleoside syn-thesis 485

Hofmann rearrangement 331 homogeneous hydrogenation 80 Hunsdiecker reaction 380 hydration of alkenes 85 -87 hydrazones, p-toluenesulfonyl-

as intermediates in conversion of ketones to alkenes 318, 319

as precursors of carbenes 307 reduction by metal hydrides 150

hydride transfer from carbon 141-143 from Grignard reagents 173-176

hydroboration 100-104 of alkynes 118, 119 asymmetric synthesis using 425, 434 with 9-borabicyc10[3.3.1]nonane 102 reviews 121

515 SUBJECf

INDEX

516 SUBJECT INDEX

hydroboration (continued) in synthesis of

alcohols 100-10 8 amines 105 ketones 105

hydrocarbons, oxidation of 393-396 hydrogena tion

of alkenes 73-81 of alkynes 11 7 catalysts for 73 homogeneous 80 reviews 121 stereochemistry 74-76

hydrogen halides, addition to alkenes 81-85 allenes 112, 113

hydrogen-metal exchange (see metalation) hydrogenolysis

of benzyl groups 76, 77 in removal of carbobenzyloxy protecting

groups 414 of thioketals 150

hydrogen peroxide epoxidation of a,,6-unsaturated ketones by 362 oxidation of carbanions by 386 reaction with nitriles 363

hydro peroxides formation from Grignard reagents and oxygen

177 in reaction of oxygen with carbanions 384-386 in singlet-oxygen oxidation of alkenes 388

a-hydroxyesters, preparation by Reformatsky re­action 181

hydroxylamine-O-sulfonic acid as source of diimide 81 in synthesis of alkylamines from organoboranes

105 hydroxymethylene derivatives 51, 52

reduction of 52 N-hydroxysuccinimide, in peptide synthesis 4 76,477 hypohalite, oxidation of ketones by 387 hypophosphorous acid, in reduction of aryl diazo-

nium ions 277

imidazole, acyl derivatives in synthesis of al­dehydes 132

imines 21 formation of by rearrangement of nitrenes 320 protonation of 43 reduction by sodium cyanoborohydride 133

iminium ion intermediates in enamine hydrolysis 22 in Knoevenagel reaction 43 in Mannich reaction 44

iminomagnesium halides, alkylation of 24 insertion reactions

of carbenes 313-316 of nitrenes 321, 322

iodides (see also halides) alkyl, synthesis via organoboranes 106 aryl, synthesis

via arylthallium intermediates 274, 275 by iodination 261-263

vinyl, synthesis via organoaluminum interme­diates 119, 120

iodination of alkenes 94 of aromatic compounds 261-263

iodine azide, as reagent 96, 97 iodine isocyanate, as reagent 96, 97 isocyanates, formation by Curtius rearrangement

330 isonitriles, reaction with organolithium reagents

420 isoprene units, introduction via reactions of 3-

methoxyisoprene 229 isotactic polymers 467 isotope effects

in chromic acid oxidation 352 in mercuration of aromatic rings 272, 273

isoxazolium derivatives, as reagents in peptide synthesis 477,478

Jones' reagent 353-355 juvabione, synthetic routes to 431-437

ketals, as protecting groups for alcohols 408, 409 glycols 410 ketones 416, 417

ketenes reactivity in 2+2 cycloadditions 219,220 from thermal decomposition of diazoketones

322-324 ketones

asymmetric reduction 424 a-chIoro-

via epoxida tion of viny I chlorides 371 by oxidation of alkenes with chromyl chlo-

ride 360, 361 a-halo-, reaction with organoboranes II 0, III halogenation of 98, 99 a-hydroxy-, by oxidation 384-386 methyl, oxidation by hypohalites 387 oxidation of 381-387

by peroxycarboxylic acids 383-385 photochemical addition to alkenes 226, 227 protecting groups for 416, 417 reaction with

Grignard reagents 171-174, 179 hydrazoic acid 333 organolithium reagents 177, 178

reduction by aluminum alkoxides 142, 143 Clemmensen reaction for 148, 149 by dissolving metals 145, 146

ketones (continued) reduction (continued)

stereochemistry of 134-138, 142, 143 stereoselective reduction by trialkylboro­

hydrides 428, 429 Wolff-Kishner reaction for 149, 150

ring expansion of, with dilizoalkanes 339,340 synthesis

of aromatic, by Friedel-Crafts reaction 267, 268

via carbonylation of organoboranes 107 from carboxylic acid chlorides and cuprate

reagents 185 from carboxylic acid chlorides and organo­

cadmium reagents 180, 181 from carboxylic acids and organolithium re­

agents 178 by mercuric-ion-catalyzed hydration of al-

kenes 114, 115 from nitriles and Grignard reagents 172 by oxidation of alcohols 351-359 by ozonolysis of alkenes 373-378

ketones, unsaturated alkylation of 18, 19 conjugate addition to 24-28 as dienophiles in Diels-Alder reaction 207,

210 enolates from 5 epoxidation of 363 photochemical cyc1oaddition reactions of 224-

226 reaction with

cuprate reagents 183, 184 Grignard reagents 176, 177 organoboranes 108-110 sulfur ylides 60, 61

reduction by lithium metal 78, 150, 151 by metal hydrides 138 selective 138, 139

synthesis from {3-diketones via enol ethers 139 via Mannich reaction 45, 46 by oxidation of alkenes 387, 388 via O!-selenoketones 100 via O!-sulfinylketones 100

{3-ketophosphonium salts, acidity of 54 {3-ketosulfoxides 52, 53 kinetic control, in enolate formation 3-6 Knoevenagel condensation 42, 45

lactones, synthesis by oxidation of cyclic ketones 385

lead tetraacetate decarboxylation of carboxylic acids by 379- 381 oxidation of ketones 382, 383 oxidative cleavage of glycols 379 reaction with alcohols 395, 396

Lewis acids catalysis of Diels-Alder reactions 209,427 in cationic polymerization of alkenes 465 in Friedel-Crafts reactions 265, 267 reaction with epoxides 370

O!-lithioaldimines 420, 421 lithium aluminum hydride, as reducing agent for

acylaziridines 132 carbonyl groups 130, 131 epoxides 139,367,368 halides 13 9-141 hydroxymethylene derivatives 52 sulfonate esters 139-141 p-toluenesulfonylhydrazones 150 trimethylsilyl ethers of cyanohydrins 339

lithium aluminum hydride-aluminum chloride combination, in reduction of epoxides 368

lithium-ammonia reduction of aromatic rings 151 epoxides 152 halides 152 O!,{3-unsaturated ketones 150

lithium diisobutylmethylaluminum hydride 120 lithium dimethylcuprate 182-187 lithium, organo-, reagents

configurational stability 168 coupling reaction with alkyl halides 170, 171 in generation of carbenes from halides 309,

310 preparation and properties 166-168 reactions with

alkyl halides 178 carbonyl compounds 177, 178 carboxylic acids 178

lithium trialkylborohydrides, as stereoselective reducing agents 428, 429

lithium triethoxyaluminum hydride, reduction of nitriles 13 3

lithium triethylborohydride 139 reaction with epoxides 367 reduction of halides 141

lithium tri-t-butoxyaluminum hydride, as selec­tive reducing agent 131, 132

'lithium, vinyl-, dimerization to dienes 190 living polymers 466

magnesium, organo-, reagents (see Grignard re­agents)

manganese dioxide, selective oxidation of al­cohols by 354

Mannich reaction 44-47 review 64

Markownikoffs rule in electrophilic addition to alkynes 114 in hydration of alkenes 86 in hydroboration of alkenes 101 in hydrogen halide addition to alkenes 81

517 SUBJECf

INDEX

518 SUBJECf INDEX

Meerwein arylation reaction 291 Meerwein-Pondorff-Verley reaction 142,358

in asymmetric synthesis 424 Meisenheimer complexes 281 mercury

alkyl derivatives of 180 aryl derivatives of 272-274 haloalkyl derivatives as carbene precursors 310,

311 salts

in catalysis of alkyne hydration 114, 115 reaction with alkenes 113 reaction with aromatic compounds 272,273 as reagents in alkene-addition reactions 87 -90

metalation 166, 167, 169 of 1,3-dithiane 419 electrophilic, of aromatic rings 272-275 of methyl vinyl ether 420

metal-metal exchange 165 in preparation of arylmercury compounds 274 in preparation of vinylcopper reagents 190 stereochemistry of 169

a-methy1eneketones, from Mannich bases 46 Michael reaction 24-28 molybdenum peroxide, oxidation of ketones

383

naphthalene, reactivity of 292-294 neighboring-group participation, in nucleoside

synthesis 486 nickel-boron, catalyst in alkene hydrogenation

77 nickel carbonyl, reactions with halides 187,188 nickel, organo-, compounds

,,-«llyl complexes 194 preparation and reactions of 187-189

nitration of aromatic rings 257-260 reviews 294

nitrenes 301 preparation and reactions 320-322 review 343

nitriles alkylation of 20 aryl

from copper-catalyzed reactions of aryl halides 288, 289

from diazonium salts 280 generation by fragmentation of oximes 329,

334-336 preparation by conjugate addition 28 reduction by triethoxyaluminum hydride 132,

133 unsaturated, preparation via alkylaluminum re­

agents 120 nitro compounds

alkylation of 20 reduction of 146

nitronic esters 20 nitronium ion, as nitrating species 258-260 p-nitrophenyl esters, in peptide synthesis 476 N-nitrosoacetanilides, as precursors of aryl

radicals 289, 290 N-nitroso compounds, as diazomethane precur­

sors 305, 306 nitrosyl chloride, addition to alkenes, 96, 97 nucleophilic aromatic substitution 275-288

copper-catalyzed 288 via diazonium ions 275-280 reviews 294

nucleosides, synthesis of 482-486 nucleotides

polymerization of 486-491 synthesis of 486-489

Nylon-6 468,473

oligonucleotides 490, 491 Oppenauer oxidation 358, 359 orbital-symmetry requirements

in carbene additions to alkenes 311, 312 in 1,3-eycloaddition reactions 216 in eycloreversion reactions 235, 237 in Diels-Alder reactions 206, 208 in sigmatropic rearrangements 226

ortho esters, thermal reaction with allyl alcohols 228

osmium tetroxide, hydroxylation of alkenes 359-361,372,373

1,3-<lxathiolanes, as carbonyl-protecting groups 416,417

oxazine, derivatives in aldehyde synthesis 24 2-oxazolines

in asymmetric synthesis of dialkylacetic acids 427,428

as protecting groups for carboxylic acids 417, 418

oxetanes, synthesis by photoeycloaddition 226 oxidation

of alcohols 351-359 of aldehydes 381-387 of alkenes 359-377, 387-393 Baeyer-Villiger, of ketones 384, 385 of carboxylic acids 379-381 of glycols 377-379 of hydrazones 306 of hydrocarbons 393-395 of ketones 381-387 of organoboranes 105 of a-selenoketones 100

oximes precursors of amides via Beckmann rearrange­

ment 328-331 reduction 146 reductive hydrolysis 417

oxirenes, as intermediates in Wolff rearrangement 323

oxy-Cope rearrangement 234 oxygen

reaction with enolates and carbanions 384-386 singlet

generation 389 reaction with alkenes 388-390

oxymercuration of alkenes 87 -90 of allenes 113 review 121

ozonolysis 373-377

palladium alkene complexes 194 salts, reactivity with arylmercury compounds

274 Paterno-Biichi reaction 226 peptides, synthesis of 472482 period ate

cleavage of <r-diketones 378, 379 cleavage of glycols 371-373, 377,378

permanganate hydroxylation of alkenes 359-361, 372, 373 oxidation of alcohols 354 oxidation of aldehydes and ketones 383-387 oxidation of hydrocarbons 394, 395

peroxytrifluoroacetic acid 370 in Baeyer-Villiger oxidation 384, 385

phenanthrene, reactivity of 292-294 phenols

base-catalyzed alkylation of 18 synthesis via arylthallium reagents 275 synthesis by hydrolysis of diazonium ions 277 thermal rearrangement of allyl ethers of 230, 231

phenyl disulfide, sulfenylation of enolates by 99 phenylselenyl halides

addition to alkenes 98 in allylic oxidation 392 in preparation of <r,i3-unsaturated carbonyl

compounds 100 phosphonate esters, in Wittig reaction 56, 57 phosphonium salts, as intermediates in ylide

preparation 54 phosphorylation of nucleosides 488490 phthalimide, in synthesis of amines 415 phthaloyl groups, as protecting groups for amines

414,415 pinacol rearrangement 336, 337 platinum, 11'-allyl complexes 195 polymerization

chain-addition 459467 coordination 460, 466 step-growth 459, 467472

polyolefin cyclization 340-343 poly phosphoric acid, as reagent for cyclization

267,268 prostaglandin, intermediates in synthesis of 443-

448

protecting groups 407418 carbobenzyloxy as 77,414,474 in nucleotide synthesis 489, 490 in polypeptide synthesis 480, 481

pseudohalogens, addition reactions of 96 reviews 121

radical anions initiation of alkene polymerization by 465 in nucleophilic aromatic substitution 291,292

radicals in chain-addition polymerization 460462 as intermediates in aromatic substitution 288-

292 as precursors of by-products in Cr(VI) oxida­

tions 353 Ramberg-Backlund rearrangement 328 Raney nickel

as catalyst in alkene hydrogenation 76 for hydrogenolysis of thioketals 150

rearrangements 322, 323 of carbene intermediates 316-319 in chlorination of alkenes 92 Oaisen 227-234 Cope 231-234 of diazomethyl ketones 323, 325 during Friedel-Crafts reactions 262-264,266 in hydrogen halide addition to alkenes 83 oxy-Cope 234 pinacol, of diols 336, 337 sigmatropic 226-234

reduction· of alkynes 115, 116 of aryl diazonium ions 277 Birch 151 of carboxylic acids with diborane 134 by catalytic hydrogenation 78, 79 Clemmensen 148, 149 of halides

with metal hydrides 139, 140 with organotin hydrides 143-145

of ketones with chiral reducing agents 424 with Grignard reagents 143, 173

lithium-ammonia 150-152 Wolff-Kishner 149, 150

Reforrnatsky reaction 181, 182 regioselectivity and regiospecificity

definition 82 in Diels-Alder reactions 208 of 1,3-dipolar cycloaddition reactions 215,216 in electrophilic addition to allenes 113 in ester pyrolysis 246 in hydroboration of alkenes 101 in hydrogen halide addition to alkenes 82 in oxymercuration of alkenes 89 of photochemical cycloaddition reactions 225 in trifluoroacetic acid addition to alkenes 86

519 SUBJECf

INDEX

520 SUBJECT INDEX

retrosynthetic analysis 430,449 Robinson annelation 35-39

using methyl I-trimethylsilylvinyl ketone, 38 ruthenium tetroxide

cleavage of alkenes in presence of periodate 372,373

oxidation of alcohols 355

Sandmeyer reaction 277-280 Schiemann reaction 280 Schmidt reaction 328, 331, 334 selenium dioxide

allylic oxidation of alkenes 390-393 oxidation of ketones 386

selenoxides elimination reactions of 98 intermediates for synthesis of unsaturated

ketones 100 selenyl halides

addition to alkenes 98 in allylic oxidation of alkenes 392 reaction with ketones 100

sigmatropic rearrangements 226-234 Oaisen 227-233 Cope 231-234

silicon, organo-, hydrides, as hydride donors 143 silver

alkene complexes 194 catalysis of hydrocarbon rearrangement 191-

193 Simmons-Smith reagent 312, 313 sirenin, synthesis of 440-443 sodium bis(2-methoxyethoxy)aluminum hydride,

as selective reducing agent 132 sodium borohydride

cleavage of trichloroacetamides by 415 cleavage of N-trifluoroacetyl groups by 475 reduction of

alkylmercury compounds 88 aryl diazonium ions 277 carbonyl groups 129, 130 oxazinium ions 24 p-toluenesulfonylhydrazones 150

sodium cyanoborohydride reduction of imines 133 reduction of p-toluenesulfonylhydrazones 150

sodium, organo-, derivatives 169 solid-phase peptide synthesis 479-482 solvent effects

on coupling of allyl halides by nickel carbonyl 188

on enolate alkylation 12-19 on rates of electrophilic addition to alkenes and

alkynes 114 step-growth polymerization 467-472 stereoregular polymers 467

stereoselectivity of addition of organometallic reagents to carbonyl

groups 179 aldol condensation 40 alkene hydrogenation 74-76 allylic oxidation by selenium dioxide 392 amine oxide pyrolysis 243 Oaisen rearrangement 230 Diels-Alder reaction 207 epoxidation of alkenes 362-365,438,439 hydroxylation of alkenes 360, 361 oxymercuration of alkenes 87 ozonide formation 375 Paterno-Biichi reaction 226 polyolefin cyclization 341 reduction of ketones 134-138,424 Wittig reaction 54-58

stereospecificity of acetoxyepoxide rearrangement 371 addition of hydrogen halides to alkenes 84 alkyl group transfer from organocuprates 187 bromohydrin formation from alkenes 94 carbene addition to alkenes 311, 312 Claisen rearrangement 230 cycloreversion reactions of azo compounds

238,240,241 Diels-Alder reaction 206, 207 1,3-dipolar cycloaddition reactions 214, 215 electrophilic substitution of organometallic

reagents 178, 179 epoxidation of alkenes 362-365 Favorskii rearrangement 326, 327 halogenation of alkenes 91 hydroboration of alkenes 103, 104 hydroxylation of alkenes 360, 361 nitrene-insertion reactions 321, 322 photochemical 2+2 cycloaddition reactions

222,223 Simmons-Smith reaction 312 thermal elimination reactions 242, 243

steric effects in alkene epoxidation 363-365 in Diels-Alder reaction 208, 209 in 1,3-dipolar cycloaddition reactions 216 in hydroboration 101-103,426 in oxymercuration 87 in reaction of Grignard reagents with ketones

173,424 in reductions with complex metal hydrides

134-138 . on stability of enamines 22

strained ring compounds rearrangement by metal complexes 191-193 synthesis

by bis-decarboxylation 380 by photochemical cycloaddition 223, 224 by ring contraction 327

styrene, polymerization of 461 sulfenyl chlorides, addition to alkenes 96 sulfolenes, loss of SO z from 237 sulfonate esters

mono-, of diols, fragmentation and rearrange­ment 335-337

reaction with Grignard reagents 171 reduction by metal hydrides 139-141

sulfones, Cl'-halo-, base-catalyzed rearrangement 328

sulfonyl chlorides, as reagents for coupling nu­cleotides 489

sulfoxides Cl'-keto-, as synthetic intermediates 100 (3-keto-, as synthetic intermediates 52, 53

sulfoximines in synthesis of oxiranes 62 in synthesis of substituted cyclopropanes 61,

62 sulfur ylides 59-63 sulfuryl chloride, in preparation of Cl'-chloro-

ketones 99 suspension polymerization 462 syndiotactic polyfners 467 synthetic equivalent groups 418-423

tetracyanoethylene as dienophile in Diels-Alder reaction 209 reaction with enol ethers 221,222

tetrahydropyranyl ethers, as protecting group for alcohols 408,409,412

thallium, aryl-, derivatives as synthetic inter­mediates 274, 275

thermodynamic control, of enolate formation 3-6

Tiffeneau-Demjanov reaction 337-339 ring contraction via 447, 448

tin, organo-, derivatives hydrides, reduction of halides by 143-145 tetravinyl, in preparation ofvinyllithium 166

p-toluenesulfonylhydrazones (see hydrazones, p- toluenesulfonyl-)

trichloroethanol acetals and ketals from, as carbonyl-protect­

ing groups 416 esters of, as carboxylic acid protecting groups

418 trifluoroacetic acid, addition to alkenes 86 trifluoroacetyl, as amine-protecting group 415,

474,475 trifluoroacetyl hypobromite, as reagent for

aromatic bromination 261 trimethylsilyl, heterocyclic derivatives in nucleo­

side synthesis 485 trimethylsilyl cyanide, addition to carbonyl

groups 339

trimethylsilyl enol ethers of esters, sigma tropic rearrangement 229 in generation of specific enolates 7, 10

trimethylsilyl ethers, as alcohol-protecting group 410

triphenylmethyl, as alcohol-protecting group 409,412

trityl (see triphenylmethyl)

Ullmann reaction 190, 191

Vilsmeier-Haack reaction 270, 271 vinylboronic esters 118 vinylcarbenes, cycliza tion to cyclopropenes

319, 320 vinyl ethers

lithiated, as nucleophilic acyl equivalent groups 419, 420

in protection of hydroxyl groups 408, 409 thermal rearrangement of 227-230

vinyl halides (see bromides, halides, iodides) vinyl sulfides, as precursors of ketones and al­

dehydes 58 Vitamin BIz' synthesis of 448

Wittig reaction 53-59 mechanism 56 phosphonate modification 56-58, 443

in synthesis of prostaglandin intermediate 444 in prepara tion of aldehydes and ketones via

enol ethers 58, 423 stereoselectivity of 54-58

Wolff-Kishner reduction 149, 150 Wolff rearrangement 323, 325 Wurtz coupling 169, 170

xanthate ester pyrolysis 246, 247

ylides carbonyl 308 phosphorus

structure 53 synthesis 54

sulfur 59-63 in synthesis of cyclopropanes 61-63 in synthesis of epoxides 60

Ziegler-Natta catalyst 466, 467 zinc

in Clemmensen reduction 148 in reduction of 4-bromomethyldioxolanes 416 in reductive removal of trichloroethyl protec-

tive groups 416, 418 zinc, organo-, derivatives

in Reformatsky reaction 181,182 in Simmons-Smith reaction 312

521 SUBJECT

INDEX