Index

Abramovici 515 Accessiblity 16 Acetalation 251 Acetic acid 81 Acetic benzoic anhydride 80 p-Acetochloroneuraminic 262 Acid anhydrides 80 Acoustic wave 370 Acridine 328 Acridone 289 Acrylate esters 345 Acrylnotirile 147 Activated methylene compounds 445 Activated oxygen carrier 177 Active catalyst 38, 39, 42, 63 Active site structure 434 Activity free energy 68 Acyl cyanides 375 Acylimidazolium salts 300 Acyltetracarbonyliron anion 353 Addition to carbon carbon-bonds 373 Addition polymers 200 Adenine 293 Adenosine 267 Adipic acid 517 Adipic acid dichlorides 213 Adipoyl dichloride 214 Adogen 464, 483 Affinity of quats to water molecules 510 Agitation rate 38, 67 Aldol condensation 255, 394 Aldol reactions 193,467-9 Aldoximes 190 Aliquat 336 (methyltrichoctylammonium

chloride) 246 Aliquat 336, 116, 520, 526, 529 Alkalation of Reissert compounds 378 Alkene epoxidation 322 Alkenylidenecarbenes 156 Alkloxide ion 61 Alkyl halides 137 Alkyl hydroperoxides 518, 522 Alkyl nitrides 24 Alkyl xanthates 120 Alkylation of macrocyclic amines 381 Alkylation of nitriles 438 Alkylation of phenylacetonitrile 433 Alkylene spacers 437 9-Alkylfluorenyl hydroperoxide 523

Alkylidene malonic acids 354 Alkyltetrazolium salts 328 Allenmark 409 Allyl bromide 38, 95, 103, 181, 185 Allyl chloride 74, 75, 181 Allyl complexes 343 Allyl phenyl ether 73 4-Allylanisole osomerization 270 Allylic alcohol 173 Allylic oxidation 519 Allylic sulfones 150 n-Allylpalladium 338 Alper 269, 354, 359 Alternating-shell model 430 Aluminium oxide 172 Alvarez-Builla 126, 286 AM 1470 AMBER 470 Amberlite IRA 904, 450 Amberlyst A27 431, 450 Ambident organic anions 18 Ambident phemolate anions 141 Amino acids 465 a-Amino acids 394 3-Aminocrotononitrile 282 3-Amino-I,2,4-triazole 293 p-Aminopropanoates 281 a-Aminomethylpyridines 280 Ammonia 532 Ammonium fluoride catalysts 469 Ammonolysis of aryl halides 532 Amount of water 39 Amphetamonium salts 113 O!-n-Amylcinnamaldehyde 193 Analgesic pentazocine 407 Analytical applications of liquid-liquid

PTe 406 Ando 371, 383, 384 Anhydrous carbonates 138 Anhydrous potassium phenoxide 438 Anhydrous solid KF 454 Anhydrous tetramethylammonium fluoride

118 Aniline 535 Anion-exchange resins 482 Anion extractability lIS Anion hydration 3 Anion transfer 9 Anionic polymerization 118

548

Anisimov 520 Anomeric nucleophilic substitutions 258 Anomeric transformations 258 Anticholinesterase agent 464 Antihistamines 178 Anti-Markonikov 179, 182 Antitumor agents 174, 175 Antiulcer agents 173 Apparent activation energy 445 Apparent binding constants 74 Aqueous film 116 Aqueous microenvironment 455 Arachidonic acid 417 Ij4-Arene-Rh complexes 347 Arbin 414 Arkopal N 419 Aromatic halogenation 519 2-Aroylbenzofurans 278 Aroyl fluorides 355 Aryl fJ-D-N-acetylglucopyranosides 262 4-(Arylamino)coumarins 295 Aryl chloromethyl sulfides 156 Aryldiazonium tetrafluoroborate 79 Aryl dichloromethyl sulfides 156 Aryl-2-furoates 298 Arylsulfonyl chlorides 345 5-Aryltetrazoles 287 Asahi Chemicals 122 Asai 535 Asymmetric alkylations 463, 466 Asymmetric isobutylation 467 Asymmetric reduction of acetophenone

476 Asymmetric synthesis 462 Atherton-Todd phosphorylation 150 Autocatalytic PTC process 381 Autoxidation of toluene to benzaldehyde

525 Auxiliary group 112 Azafluorene 295 Azaleic acid 517 Aziridines 277, 286, 378 Azobenzenes 328, 358 Azobisisobutyronitrile 471 Azoisoheptanenitrile 186, 238 Azoxybenzenes 328, 520

Baeyer-Villiger oxidation 455, 519 Baker-Venkataraman reactions 279 Barbituric acid 293 Barium hydroxide 115 Bartsch 437 Base-catalyzed isomerization 396 Base-catalyzed transesterifications 395 BASF 122 Batch reactor 101 Becker 250 Benyltriethylammonium chloride 210

INDEX

IH-3-Benzapines 282 Benzene effect 19 Benzene-1,4-dimethanol 223 Benzenecarboxylic acids 324 Benzimidazole 292 2-Benzimidazolone 279 Benzimidazol-2-one 292 Benzoate 170 Benzoate ion 80, 86, 88 Benzodiazepin-2-one 293 Benzofluroxane 285 Benzoic acids 517 Benzoic anhydride 80 Benzoisothiazoline 195 Benzonitrile 27 Benzonitrile tetrachloromethane 80 Benzooxazines 276 Benzophenone imine 303, 466 Benzotriazepines 287 Benzothiazepinone 290 Benzotriazole 293 Benzoxazines 278 Benzoyl chloride 80, 85, 189,247, 535 Benzoyl chloride phenylimnine 287 Benzoyl cyanides 23, 189 Benzoyl isothiocyanate 189 Benzoylpyridinium chloride 535 Benzyl 2-acetamido-6-0-benzyl-3-0-[(S)-I­

carboxyisopropyll]-O(-D-glucopyranoside 250

Benzyl bromide 93, 171 2-Benzyl-I-bromo-I-chlorocyclopropane 156 Benzyl chloride 169, 339 Benzyl cyanides 27, 84, 170 (Z)-3-0-benzyl-5,6-dideoxy-1 ,2- 0-

isopropy lidene-6-phenyl-0(-D-xylohex-5-enfuranose, 256

Be~zyl esters 170 Benzyl fluoride 21 Benzyl quaternary ammonium salts 169 Benzyl thiols 190 Benzylation of sucrose 245 2-enzylbenzoxazoles 295 Benzylcinchoninium halides 112 Benzylidene halides 156 Benzylidenemalononitrile 281 (-)-Benzylquininium chloride 129 Benzyltributylammonium chloride 184 Benzyltri-n-butylphosophonium 93 Benzyltri-n-butylphosphonium ions 433 Benzyltributylphosphonium chloride 491 Benzyltriethylammonium chloride 204,

207,212,225,226,249 Benzyltrimethylammonium 93 Benzyltrimethylammonium bromide

(BTMAB) 486 Benzyltrimethylammonium dichloroiodate

534

INDEX 549

Benzyltrimethylammonium tetrachloroiodate (BTMAICI4 ) 534

Benzyltrimethylammonium tribromide 194 Benzyltriphenylphosphonium bromide 257 Benzyltriphenylphosphonium chloride 225 Berthelot 533 Billerit 278 Biphasic glycosylations 265 Biphasic hydroformylation 538 4,4'-Biphenol 207 4,4'-Biphenyldithiol 229 Bis(acetylacetonato )nickel(I1I) 321 1,4-Bis(bromomethyl)benzene 206, 222,

230 1,3-Bis( carboxypropyl)tetramethy 1-

disiloxane 235 1,4-Bis( 4-chlorobenzoyl)benzene 209 I ,3-Bis( 4-chlorobenzoyl)-5-tert-

butylbenzene 209 2,2-Bis( 4-chloroformylphenyl)propane 216 1,4-Bis(chloromethoxy)butane 205 1,4-Bis( chloromethyl)benzene 206 I ,4-Bis( chloromethyl)2,5-dimehtoxy-

benzene 207 3,3-Bis( chloromethyl)-oxacyclobutane 203 3,3'-Bis( chloromethyl)-oxacyclobutane 216 3,3-Bis(chloromethyl)oxetane 232 Bis( 4-chloro-3-nitrophenyl)sulfone 208,

231 Bis-(dialkylaminopyridinium)salts 299 Bis( 4-dihexylaminopyridinium )decane

dibromide 126 Bis(2,4-dinitrophenyl)carbonates 220 1,8-Bis(ethynyl)naphthalenes 353 Bis(guanidinium) salts 126 Bis(4-hydroxyphenol)ether 212 1,4-Bis(hydroxymethyl)benzene 223 3,3-Bis(4-hydroxyphenyl)butanoic acid 227 Bis(4-hydroxyphenyl)ether 209 9,9-Bis( 4-hydroxypheny 1)-fluorene 213 2,2-Bis( 4-hydroxyphenyl)-I, I, I ,3,3,3-

hexafluoropropane 213, 234 Bis(4-hydroxyphenyl)ketone 202 I, I-Bis( 4-hydroxyphenyl)-4-

methylcyclohexane 216, 217 3,3-Bis( 4-hydroxyphenyl)pentanoic acid

227 1,1-Bis( 4-hydroxyphenyl)phenylethane 20 I 2,2-Bis( 4-hydroxyphenyl)propane 20 I 2,2-Bis( 4-hydroxyphenyl)propanoic acid

227 Bis(4-hydroxyphenyl)sulfide 202 Bis(4-hydroxyphenyl)sufone 202, 206, 209 Bis(4-hydroxyphenyl)thioether 209 Bis(indazolyl)methanes 291 Bis(4-mercaptophenyl) sulfone 218 Bis[ methyl]-2,3- O-methylene-fJ-D-

ribofuranosid-5-yloxymethane 252

Bis(2-nitrophenyl)carbonates 219, 220 Bis(4-nitrophenyl)carbonates 220 1,4-Bis(4-nitrophenyl carbonate )-cyclohex-

2-ene 223 Bisphenol 184, 223 Bisphenol A 201, 202, 204, 207, 234 Bisphenol AF[2,2,-bis(4-hydroxyphenyl)-

1,1,1,3,3,3-hexafluoropropane] 224 Bis(phthalimide)sulfides 186 Bis-stilbenes 182 Bis(2,4,6-trichlorophenyl)carbonate 219,

220 Blossey 482 Blum 348, 349, 352 Boc-Ieucine 483 Bodor 122 Boileau 483 Bonnemann 527 Bormoform 155 Bornyl 2-bromocarboxylates 477 Borohydride reductions 476 Boron trifluoride 120 Bosch 514 Boutonnet 526 Bram 8 Brandstrom 2, 4,17,18,37,56, III, 114 3-Bromoacetyl-I, I'-dimethylferrocene 415 4-(p-Bromoacetylulphenyl)butanoic acid

215 Bromobutane 435, 438, 444 4-Bromo-2,6-dimethylphenol 210 9-Bromomethylacridine 420 3-Bromomethyl-7-methoxy-1 ,4-benzoazin-

2-one 417 4-Bromomethyl-7-methoxy­

coumarin(Brmmc) 419 4-Bromomethy 1-6, 7 -methylenedioxy-

coumarin(Brmmdc) 416 I-Bromooctane 93 I-(Bromophenyl)-ethyl 513 1-Bromo-propane 179 I-Bromo-2,3,5-tri-O-benzyl-D-

arabinofuranose 266 I-Bromo-2,3,5-tri-O-benzyl-D-ribose 266 (-)-Brucine 304 Brunelle 28, 125, 127,219,299 Burdett 528 Butane-I,4-dithiol 483 Butan-I-ol 60 Butanoyl chloride 88 Butatriene 383 Butchalor 187 Butobarbintone 293 Butorphanol 176 Butyric acid 407

C-alkylation 18, 141 C-anions 490

550

Calcium fluoride 514 Calcium hydroxide 115 Camphorimide 288 Cantrell 125 Carbamoylazides 298 Carbazole 289, 483 Carbodimides 177 Carbon acids 531 Carbon dioxide 511 Carbon disulfide 145, 227, 250, 280, 294 Carbon-nitrogen bond formation 477 1,2-Carbonyl additions 469 Carbonylation 180, 351, 525 Carbonylation of benzyl chlorides 360 Carbonylation of bromobenzene 355 Carbonylation of terminal alkynes 362 Carpino 531 Catalyst conditioning 433 Catalyst deactivation 115 Catalyst loading level 440 Catalyst particle size 94, 433, 441 Catalyst recovery and recycle 127 Catalyst separation 169 Catechol 179, 250 Cationic ring-opening copolymerization

436 Cavitation 370 CD-PdCb system 271 Cellulose 268 Cerichelli 534 Cetylpyridinium chloride 365 Cetyltributylphosphonium bromide 527 Cetyltrimethylammonium bromide

(CTAB) 253, 420, 534 Cetyltrimethylammonium hydroperoxide

119 Chao-Shun 308 Chaudhary 195 Chela ton 385 Chemical derivatizations in analytical

chemistry 406 Chemical effects of cavitation 371 Chemical modification of polymers 480 Chemically modified cyc10dextrins 269 Chen 408 Chiba 515 (+ )-Chinchonine 325 Chiral IX-hydroxy ketones 327 Chiral ammonium fluoride 469 Chiral crown ether 465-6, 469 Chiral epoxides 284 Chiral macrocyclic crown ethers 250 Chiral quats 169 Chiral trans-epoxides 472 IX-Chlorination of ethyl benzene 516 2-Chloroacetanilide 280 Chloroacetylene 147 IX-Chloroalkaneitriles 144

INDEX

ChI oro benzene 61 I-Chloro-2-deoxy-3,5-di-O-p- toluoy I)-IX-D-

erythro-pentofuranose 266 I-Chlorododecane 21 IX-Chloroethyl carbonate 31 Chloroform 25, 155 Chloro(I ,5-hexadiene )rhodium(I) 270 8-Chloro-5-methoxy-2-methyltetralone 474 2-Chloromethylfuran 298 Chloromethylated polystyrene 481 4-Chloro-N-methylphthalinide 186 2-(Chloromethyl)pyridine 250, 298 4-Chloromethylpyridine 175 Chloromethylstyrene 451 Chloromethylthiirane 298 2-Chlorophenothiazine 289 Chloroprene 196 6-Chloropurine 528 6-Chloropyridin-2-01 192 Chloropyriphos 187 Chlorotrimethylsilane 251 Chlorovinylidenecarbene 157 Cholesteryl glycoside 262 Christie 118 Chromium (III) N' ,N,-ethylenebis(salicyl-

ideneaminato) (salen) 270 Chromones 278 Cinchona alkaloids 112, 467 Cinchonidine 30 I, 465 Cinchonine 301, 463, 465, 474 Cinchoninium bromide 467 Cinnamyl alcohol 326 Cis-addition 344 Cis-I,4-dichlorobut-2-ene 204 Cis-dichlorobis( dimethylphenyl-

phosphine)platinum 240 Cis-elimination 344 Cis-glycols 323 Cis-inositol diol 248 Cis-stilbene 71 CI electrophiles 149 Clark 531 Classification of triphase catalysis 425 Clathrate formation 511 Cleavage of styrene to benzaldehyde 521 Cobalt chloride 525 Cobalt chloride-potassium cyanide system

356 Codeine 176 Colloidal rhodium 349, 527 Colonna 302 Column chromatography 50 Concentration of catalyst 19 Condensation polymers 29, 200 Condensed imidazole derivatives 280 Continuous-flow reaction 457 Conversion of epoxides to fluorohydrins

514

Copoly(carbonate thiocarbonate) 235 Copoly( ester-carbona te) 234 Copolymers 231 Corral 380 Coulombic interactions 434 Coumarins 278, 296 Cousseau 514 Cross-linked polystyrene 433 Cross-linking 93, 94, 96 Cross-linking level 440 15-Crown-5(15-C-5) 485 18-Crown-6 191, 222, 267, 416, 483 19-Crown-6 414 Crown ethers 3, 21, 169 Cryptand[2.2.2] 483 Cryptons 5 Csanyi 520 Cyanation of bromooctane 431 Cyanide ion 374 Cyanoethyl acetate 178 f3-Cyanoethyl ethers 374 Cyanohydrin esters 375 Cyanohydrin reactions 255 Cyanotetrahydrothiophenes 277 Cyanotricarbonylnickel(O) 364 Cyanotricarbonylnickelate anion 360 Cyclic f3-keto esters 397 Cyclic state 13 Cyclic trithiocarbonates 382 Cycloaddition of diphenylnitrilimine 398 Cycloalkylammonium salts 299 Cyclodextrins 268, 536 Cyclohexen-I,2-diol 520 Cyclohex-2-en-l-one 523 Cyclomaltohexaose 269 Cyclo-oligomerization of alkynes 350 Cyclopent[a]acenaphthylenone 353 Cyclopent-2-enone 471 Cyclopropanation 256 Cyclopropane carboxamide 179 Cypermethrin 187 Cytochrome P-450 model compounds

283

D-galactosides 246 f3-D-galactoside epimer 256 D-g1ucosides 246 D-mannosides 246 Damkoh1er numbers 48, 95 Darzen reaction 193 Darzens condensation 144,471-2 Davidson 380 De Ruiter 410 Dealkoxycarbonylations 396 Debromination-hydroxylation reaction

354 Decanoic acid 407 Decomposition of anions 120

INDEX

Decomposition of hydro peroxides 523 Deethylation 400 Degradation of catalyst 19 Degree of aggregation 9 Degree of association 17 Degree of dissociation 74 Degree of esterfication 486 Degree of ring substitution 441 Degrees of elimination 496

551

Dehmlow 8, 16, 113, 122, 177, 194, 299, 304, 518

Dehydration 511 Dehydrobomination 188 Dehydrofluorination of poly(vinylidene

fluoride) 498 Dehydrogenation 349 Dehydrohalogenation 184 Demethylation 399 Deng 393 2-Deoxy-2-acetamido-sugars 261 2-Deoxy-2- 18 Flfluoro-D-

glucose([ISFlFDG) 456 2-Deoxy-l-halopentose 265 Deprotonation 136 Deprotonation at carbon atoms 376 Deratani 269 Dermeik 511, 514 Des Abbayes 339, 353 Desulfurization 471 Desulfurization of oils 521 Di Cesare 251 1,4-Diacetyl-2,5-piperazinedione 294 Dialkoxymethane 58 Dialkoxythiophosphoryl chloride 187 4-Dialkylaminopyridinium salts 299 I, 1'-Dialkyl-4,4'-bipyridinium salts 308 Dialkyl malonate 179 1,4-Diamino-2,3-dichloroan thraq uinone

183 1,3-Diaminopropane 435 2,6-Diamino-purin-8-ol 240 Diaryl ethers 28 Diarylbutadiynes 345 Diarylcarbodimides 285 Diazabicyclo-[5.4.0]undec-7 -ene (DBU)

504 Diazinon 187 Dibenzo-18-crown-6 202, 416 Dibenzol-I,3,6,8-tetraoxocine 276 Dibenzosuberone 171 Dibenzyl ether 171 Dibenzyl sulfide 171 Dibenzyl sulfone 171 Gi-p-Dibromoacetophenone 414 1,4-Dibromobutane 444 1,4-Dibromobutyne 382 Dibromodifluoromethane 158 1,7-Dibromoheptane 210, 231

552 INDEX

1,6-Dibromohexane 202 Dibromomethane 59, 60, 61, 66, 158,201 4,4'-(Dibromomethyl)benzophenone 214 4,4'-(Dibromomethyl)diphenyI214 1,9-Dibromononane 231 1,5-Dibromopentane 231, 232 2,4-Dibromophenol 533 Dibutanoxymethane 59 Dibutyl ether 61 Dibutylin oxide 267 cx,cx-Dichloroadipic acid 517 2,4-Dichlorobenzyl alcohol 171 3,4-Dichlorobut-l-ene 184 DichlorocycIopropyl sugars 258 1,8-Dichloro3,6-dioxaoctane 250 3-(2,2-Dichloroethenyl)-2-

dimethylcycIopropanecarboxylic acid chloride 187

1,6-Dichlorohexane 185 Dichloromethane 201 Dichloromethyl ketones 154 Dichloromethyladmantane 154 Dichloromethylethyne 157 3,5-Dichloro-cx-methylstyrene 188 2,3-Dichloronaphthoquinone 281 3,4-Dichloronitrobenzene 531 1,5-Dichloro-3-oxapentane 250 1,I-Dichloro-2-phenylcycIopropane 153 4,6-Dichloropyrimidines 173 2,3-Dichloroquinoxaline 281 2,3-Dichloroquinoxaline-I ,4-dioxide 281 1,6-Dicyanohexane 196 Dicyanostilbene 149 DicycIohexane-18-crown-6 206, 208, 318 DicycIohexyl-18-crown-6 (DCHC) 483,

414,416 DidecycIdimethylammonium bromide 172 Didecyldimethylammonium bromide

(DDAB) 516 Dielectric constants 17, 18, 61 Diethyl acetamidomalonate 306 Diethyl methylmalonate 484 Diethyl zinc 469 Diethylaniline 82 2,6-Diethyl-3-cyano-4-oxopyran 282 2,6-Diethyl-3-cyano-4-oxothiopyran 282 2,6-Diethyl-3-cyano-4-thioxothiopyran 282 Diethylene glycol bischloroformate 223 Diffusion coefficient 95 Difluorocarbene 157 DifluorocycIopropanes 158 7,7-Difluoro-l-methylbicycIo[4.1.0]heptane

158 Diglycidyl glutarate 520 cx,w-Diglycidyloligo(oxyethylene)s 438 cx,w-Dihaloalkanes 139 Dihalocarbenes 151, 155 1,4-DihydroxycycIohex-2-ene 223

DihalocycIopropanes 155 Dihexyltetramethylguanidinium bromide

130 Dihydrodibenzazepine 174 2,3-Dihydro-5-hydroxyindole 296 Dihydrolysergic acid 176 1,2-Dihydroquinoline 289 2,3-Dihydro-3-(substituted amino)-IH-

isoindol-I-ones 289 Dihydrouracils 281 4,4'-Dihydroxy-cx-methystilbene 203, 205,

231 2,6-Dihydroxyanthra aquinone 208 4,4'-Dihydroxyazoxybenzene 202 4,4' -Dihydroxybenzophenone 206 4,4'-Dihydroxybiphenyl 202, 216, 231, 240 p-Diketones 531 Dimensioned waveguides 389 Dimethyl malonate 237 Dimethyl sulfate 191 Dimethyl sulfoxide 440 2,4-Dimethyl-2-aminopentanenitrile 186 4-(Dimethylamino)pyridine 219 4-Dimethylaminopyridine (DMAP) 220,

227, 535 5-Dimethylamino-l-sulphonyl chloride

(dansyl chloride) 410 Dimethylcantharidic acid 288 2,5-Dimethylhexane-2,5-diol 223 1,2-Dimethylindole 289 Dimethylpyrazines 328 4,6-Di-O-acetyl-2,3-0-carbonyl-cx-D-

mannoppyranosyl bromide 262 Dioctadecyldimethylammonium chloride

(DDAC) 526 Diol-containing polyetheramine 439 1,2:3,4-Di-O-isopropylidene-cx-D-

galactopyranose 262 1,3-Dioxoalkanes 295 1,3-Dioxolane 277 1,4-Dioxolane 281 Diphenols 201 Diphenylamine 142 4,4'-Diphenyldicarboxyl dichloride 216 3,5-Diphenylpyrazoles 291 Dipole movement 61 Dipole-dipole bond 61 Dipotassium cycIohexane-I,4-diolate 222 1,3-Diselenols 282 Dismutation of H202 519 Dismutation of hydrogen peroxide 522 Disodium 4,4'-oxydibenzenesulfinate 230 Disproportionation 349 Disproportionation of cycIehexa-1 ,3-diene

525 Distribution coefficient 43, 64, 73, 78 Distribution of ions 2 Ditetrabytylammonium L-tartarate 186

Dithiocarbonates 250 1,3-Dithiol-2-thione 280 Do 517 Dobemzazepine 174 Docosahexanoic acid 417 Dolling 302, 304 Double alkylation 276 Double asymmetric induction 477 Double carbonylation 361 Dovganyuk 520 Dow 536 DSM 538 Durst 414 Dynamic behaviour 43

Effectiveness factor 94, 457 Egawa 503 Ehrsson 406 Electroconductance 74 Electrolysis 118 Electron transfer catalysis 308 iX-Elimination 151, 155 p-Elimination 158-60, 399 1,3 Elimination 157 p-Elimination of alkyl halides 513 Elimination reactions of polymers 496 Elimination reactions of PVC 497, 498 Enantiomeric efficiency 463 Enantioselective ketone reductions 269 Enantioselective phase transfer reactions

112 Enantioselective synthesis 465 Enantioselective trifluoromethylation

469 Enhanced selectivity 168 Enthalpy of activation 69 Entropy of activation 69 Ephedra alkaloids 462 Ephedrine 301 (-)-Ephedrine 475 (+ )-Ephedrine 469 Ephidrinium salts 113 Epichlorohydrin 185,204, 205 Epoxidation of alkenes 365 Epoxidation of chalcones 456, 474 Epoxidation of oct-I-ene 521 Epoxidations 112 Epoxides 357 Epoxy alcohols 357, 365 Equilibrium model 63 Equivalent conductance 74 Ester hydrolysis 374 Ester saponification 395 Estradiol 412 Estradiol-17B 175 Estramustine 175 Esumi 526 Ethambutol 179

INDEX

Ethoxycarbonyl cyclopropane 141 Ethyl acetate 82 Ethyl bromoacetate 452 Ethyl croton ate 249 Ethyl cyanoacetate 236, 378 Ethylene dibromide 378 Ethylenebis( l-bromo-l-ethoxyacetate)

215 2-Ethylhexaldehyde 193 2-Ethylhexene-l,3-diol 190 I-Ethyl-4-picolinium salts 295 2-Ethynyl-2-phenylpropionitrile 147 Eugenol 396 Evans 127 Exhaustive alkylation III Expulsion of hydrogen halides 527 External mass transfer resistance 106 Extraction of base 529 Extraction competition 139 Extraction constant 2, 6, 17 Extraction efficiencies 408 Extractive alkylation 37, 409 Eyal 514

Factors affecting activity of triphase catalysis 429

Falling-drop experiment 2 Fell 538 Fenvalerate 171 Fenvalerate 188 Fiaud 302 Fife 535 Film diffusion 97 Finkelstein conditions 298 Finkelstein reaction 513 Fixed-bed reactors 457 F1avanoid glycosides 260 Flavones 278 Flavonoid glycosides 262 Florisil 195 Fluorene 320 Fluorescence detection 409 Fluorescent brighteners 183 5-Fluorocil 295 5-Fluororacil 293 Fluorodenitrations 127 Foramaldehyde acetals 59 Ford 93, 94 Foreign anion 114 Formaldehyde 193 Formate salts 338 9-Formylacridine 298 Fort 520 Fractal number 372 Frechet 483 Freedman 517 Freeze crystallization 50 Friedel-Crafts alkylation 79

553

554 INDEX

Fumaric acid 239, 326 Furfural 326

Gabriel reaction 476 Galamb 354 Gallo 291, 511 Gannon 324 Gasparrini 329 Gedye 386 Gel permeation chromatography 203, 213 Gem-dibromocyclopropanes 360 Gem-dichlorocyclopropanes 154 Gem-dihalocyclopropanes 160 General electric 125 Gibson 482 Giguere 386 Gingras 127 Glucuronic acid metabolites 260 Glutaric acid 517 Glutarimide 288 Glutathione-S-transferases 193 Glycidyl methacrylate 520 Glycidyl methacrylate copolymers 435 Glycine 178, 465 Glycoconjugate chemistry 260 Glycohydrolase enzyme substrates 260 Glycolsylations 267 Glycopeptides 260 Glycosyl cyanide 265 Glycosyl phosphates 260 Glycosyloxtsuccinimides 260 Glycosyloxybenzotrialzolides 260 Gokel 18,27 Gold colloidal solutions 527 Goldberg 265 Goldberg amide arylations 345 G6zdz 483 Grasbarski 303 Guanidinium salt catalysts 528

Halex reaction 125, 127 Halide exchange 182 9-Haloanthracene 347 a-Halocarbanions 135, 148 2-Haloethylbenzene 439 Halogen exchange 260 Halo hydrido transition metal complexes

342 x-Halonitriles 157 1-Halopentoses 265 a-Halo-sugar 258 Hansch n-hydrophobicity constants 15, 16 Harustiak 524 Heck reaction 282 Heck-type reactions 344 Heiszmann 178 Heliotropine 179 Heroguez 502

Heteroanions 141 Heteroarylchlorocarbenes 156 Heteroatom electrophiles 149 Heterocyclic ammonium salts 299 Heteropoly acids 319, 365 Hexaalkylguanidinium salts 126 Hexachlorocyclo hexane 513 Hexachlorocyclotriphosphazene 49 Hexachlorotriphosphazene 95 Hexadecyltributylphosphonium bromide

207, 256 Hexadecyltrimethylammonium bromide

207, 498 Hexadecyltrimethylammonium chloride

212 Hexamethylphosphoric triamide 318 Hexathylguanadinium chloride 126 Hexfluorobenzene 209 Hexppyranoside-4,6-diols 248 9-Hexyfluorene 325 Hexyltrimethylammonium bromide

(HTMAB) 486 High-speed stirring 19 Hill 520 Hiroshi 181 Hoechst 31 Hofmann 112 Hofmann degradation 123, 124,463 Hofmann elimination 20 Hofmann rearrangement 179, 194 Horner-Emmons reaction 194 Hot spot theory 370 HSAB principle 290 Huang 327 Hughes 38, 307 Hydantoin 280 Hydration of acetylenes 525 Hydration shell 5 Hydration 4, 5 Hydrazoic acid 118 Hydrobromic acid 513 Hydrofluorination of activated acetylenes

514 Hydroformylation process 537 Hydrogen cyanide 515 Hydrogen fluoride 514 Hydrogen peroxide 319,518 Hydrogen sulfate 511 Hydrogen transfer 349 Hydrogenation of activated double bonds

347 Hydrogenolysis 338, 339, 346 Hydrognation of aromatics 348 Hydrolysis of aromatic nitriles 519 Hydroperoxides 141 Hydrophilic balance 440, 443 Hydrophilicity of the catalyst 98 Hydrophobic cavity 270

I-Hydroxybenzotriazole 295 Hydroxychromones 296 4-Hydroxydithiocoumarin 296 Hydroxyethyl carboxylates 327 Hydroxylamine 503 a-Hydroxylation of ketones 112, 474 3-Hydroxymethylisoftavones 278 Hydroxymethylquinuclidine 468 3-Hydroxyphenyl- 3-hydroxybenzoate 223 3-Hydroxyphenyl-4-hydroxybenzoate 223 3-(4'-Hydroxyphenyl)-I,I,3-trimethyl-4-

indanol 226 3-(4'-Hydroxyphenyl)-l, I ,3-trimethyl-4-

indanol221 3-(4'-Hydroxyphenyl)-l, I ,3-trimethyl-5-

indanol 210, 212, 213, 233 5-Hydroxypyrazoles 295 4-Hydroxyquinoline 296 4-Hydroxyquinolin-2-one 290 Hypochlorite oxidation 189 Hypochlorite 172,318, SIS Hypochlorous acid 516

Ibuprofen 181, 195 Imidazole 291-2, 322 Immobilized quaternary ammonium salts

103 In situ generation of hypochlorite 517 Indanone 469 Indoles 142, 287 2-Indolinone 294 Indolizine 286 Indomethacin 414 Induction period 38, 46 Industrial processes 168 Inhibition 139 Interfacial mechanism 136 In terfacial region 136 Interphase polycondensation process 212 Intramolecular H-bonding 529 Intraparticle diffusion 428, 442, 445 Intraparticle diffusion limitations 94 Intraparticle effectiveness factor 106 Intrinsic rate constant 56 Intrinsic reaction rate 43, 58, 96 Intrinsic reactivity 94, 434, 441 Inverse phase transfer catalysis 79, 268,

307, 535 Inverted micelles 522 Iodide 408 Iodosylbenzene 270, 321 Ion exchange resins 195 Ion exchange 25, 428 Ion-exchange rate 445 Ion extraction mechanism 77 Ion pair 56 Ion pairs 17, 18, 62 Ion-pair extraction 159

INDEX

Ion-pair extraction mechanism 77 Ion pair partition 37 Ion-selective electrodes 2 Iron ylide complexes 339 y-Irradiation 438 Irreversible kinetic behaviour 91 Ishii 365, 519, 520

555

'Ishii-Venturello' epoxidation reaction 520 Isobutanal 171 Isoeugenol 396 Isomerization 349 Isophthalic acid 212, 234 Isophthalic acid dichlorides 211 Isophthaloyl dichloride 211, 218 2-Isopropyl glycidonitrile 144 4,4'-Isopropylidenedibenzenethiol 227 Isopropylidene malonate 452

Jacobsen 473, 477 Jain 278 Jarousse 36 Jeffery 344 Jovanovic 179 Julia 302, 455

Kajigaeshi 533 Karakhanov 521 Ketene dithioacetals 145, 294 a-Keto acids 408 Kim 252 Kise 497 Knoevenagel condensation 143 Koch 178 Koenigs-Knorr glycosidation 263 Krapcho conditions 398 Krbechek 191 Krishna Kumar 185 Kryptofix 222, 416 Kumala 190 Kuneida 271 Kuo 535

L-L-S Triphase reaction system 427 L-xyloaldehyde 257 f3-Lactans 277 Landini 3, 5, 54,114,121,123,512-14 Landre 348 Large-ring lactones 454 La ttice energy 6 Lattice-free ions 13 Leaving group 9 Lee 517 LePerchec 127 Ligand exchange 343 Lignin 185 Lin 195, 339 Liotta 4, 8 Lipophilic balance 440, 443

556

Lipophilicity of the catalyst 441 Lipowitz 305 Liquid crystals 231 Liquid-liquid anion exchange 113 Liquid-liquid systems I Liquid membranes 2 Liquid-solid system 30 Lissamine Rhodamine B sulfonyl chloride

(1 aryl chloride) 412 Lissel 126 Long-chain ammonium salts 123 Loupy 22, 306 Lu 194 Lysergic acid 176

m-nitroanisole 28 m-phenoxybenzaldehyde cyanohydrin 187 Macroporous butyl acrylate-DVB

copolymers 435 Macroporous pellet 98 Macroporous polystyrene resins 449 Macroporous trimethylbenzylammonium

catalysts 449 Maggioni 179 Magnetron 389 Maitlis test 527 Makosza 27, 37, 114, 173, 369, 409, 532 Malononitrile 237 Mandelic acid 189 Manganese porphyrins 283, 521 Mank 417 Maolnonitrile 484 Mason 380 Mass Biot number 101 Mass-transfer 37 Mass-transfer catalyst 43 Mass transfer coefficients 43-5, 53, 58 Mathias 307, 535 McElligot 520 McKillop 37 McLain 338 Mean particle size 433 Mechanical stirring 19 Mehschutkin reaction III Melt polymerization 219 Membrane-supported quaternary

ammonium phase transfer catalyst 518 Menscgutkin 112 Menthoneimine 303 Merck catalyst 464, 470 Merck method 464 Merrifield 482 Mesutiuc esters 395 Metal colloidal catalysts 526 Metamitron 189 Methergoline 176 4-Methoxy-I H-pyrazolo[3,4-dJpyrimidine

266

INDEX

Methyl 4,6-0-benzylidene-ac-D­glycopyranosides 246

Methyl 2-0-acetyl-4,6-0-benzylidene-3-deoxy-3-ni tro-P-D-glucopyrannosides 256

Methyl acrylate 469 Methyl chloroacetate 187 Methyl cyanoacetate 237 4,4'-Methylenebis(2,6-dimethyphenol) 212 Methyl-L-rhamnopyranosides 246 Methyl mandelate 189 Methyl phenylacetate 470 Methyl 2-phenylpropionate 469 3-Methyl-l-phenyl-5-pyrazolone 291 Methyl vinyl ketone 469 rx-Methylamino acids 465 Methylated P-CDs 271 Methylene-dioxybenzene 179 Methylenedioxybenzene 179 2-Methyl-4(5)-imidazole 292 Methylnaphthalenes 325 4-Methyloxatole-5-carboxyethyl 177 Methylpyridines 325 Methyltriethylammonium iodide (MTEAI)

483 Methyltrioctylammonium bromide

(MTOAB) 486 Methyltrioctylammonium chloride 206 4-Methylumbelliferyl ketoside 262 Micellar phase transfer catalysis 419 Michael acceptor 149 Michael addition 255, 295, 302, 465, 469 Michael reactions 112, 147, 193 Microporous (gel) catalyst 449 Microporous pellet 98 Microporous resins 449 Microwave activation 386 Microwave chemistry 385 Minoura 482 Mixed halo forms 155 Mixed halogen cyclopropanation 377 Mixed phosphorous ylides 339 Mixed sulphur ylide 339 Mn(III) tetraphenylporphyrin complex

321 Molecular connectivity 15 Molecular oxygen 319 Molecular recognition 465 Monflier 537 Monoalkylation 138 Monobromination of thiophene 534 Monocrotophos 191 Monodispersed colloidal metal particles

526 Monosaccharides 246 Monsanto 183 Montanari 444 Mori 483

INDEX 557

Morphine 176 Morphology of polymer support 448

3-[ N-4-acetyl )pheny lcarbamoyl]-2,5-NBD-2-carboxylate 501

N-alkylation 173, 291 N-alkylation of hexamtherylenetetramine

532 N-alkylation of saccharin 394 N-alkylbenzimidazoles 292 N-alkylbenzoxazinones 290 N-alkyl-N;N'-dialkylaminopyridinium 125 N-alkylpiperidines 277 N-alkylpyrazoles 290 N-alkyl-2-pyridones 290 N-anions 488 N-aryl-N-aroyl-N'-arylcarbamidic azide

285 N-arylation 291 N-arylpyrazoles 291 N-benzoylbenzimidazole 294 N-benzoyluracil 293 N-benzyl-N-N-dimethyl-N-alkyl-

ammonium chloride 169 N-benzylcinchonidinium chloride 294, 303 N-benzylcinchonidinium 303 N-benzylcinchoninium 302, 303 N-benzylcinchoninium fluorides 303 N-benzylquinidinium chloride 519 N-benzylquininium salts 303 n-butyl bromide 179 n-butyldiethyl malonate 179 n-butytraldehyde 193 N-carbobenzyloxy-L-valine 482 N-carboxyl-L-alanine anhydride 456 N-2-chloroethyloxyethylpyrazoles 291 N-I,2-dichlorovinyl carbazole 289 N-ethoxycarbonylnorcodeinone 176 N-ethylcarbazole 79 N-(2-ethylhexyl)-4-dimethylamino-

pyridinium chloride 129 N-ethylphenothiazine 289 (-)-N-(9-fluorenyl)quininium Bromide 130 n-heptanal 193 n-hexadecyl trimethylammonium bromide

408 n-hexane 205 N-methylacridones 290 N-methylephedrinium salts 302 4-N-methylmorpholine N-oxide 321 N-methylpyrrolidone 236 N-methylpyrrolidone 440 N,N-Bis(2-chloroethyl)carbamoyl 175 N,N-dialkylacrylamide 436 4-N,N-dialkylamino)pyridinium salt 456 N,N-dialkylated D-glucosamine 253 N,N-diethyl-2-(dimethyl-

sulfuranylidene )acetamide 258

N,N-dimethylacetamide 210, 440 4-N,N-dimethylamino )cinnamate 498 N,N-dimethylaminobenzophenone 502 N,N-dimethylamino pyridine 80 N,N-dimethylformamide 440 n-octyl bromide 536 n-octyl methansulfonate 444 N-(p-nitrophenyl)imidazole 292 N-polypyrazolylmethanes 291 N-propargylated 290 N-propargylbenzimidazole 292 N-sulfonylazepines 284 (+)-N-(4-trifluoromethyl)benzyl-

dihydrocinchonium bromide 130 Naganuma 415 Naloxone 176 Naltrexone 176 2-Naphthacyl bromide 409 2-Naphthacyl esters 409 2-(2,3-N aph thalimino )ethyl

trifluoromethanesulfonate 417 Narasimhan 527 Negative-type photoresists 498 Neumann 172,384,518 NH acids 142 Nicergoline 176 Nickel tetracarbonyl 359 Nickel-catalysed carbonation 359 Nishikubo 482, 505, 530 Nitrene 378 Nitric acid 321, 329 Nitrides 23 Nitrite 408 4-Nitroaniline 183 Nitroarylation 27, 148 4-Nitrobenzaldehyde 178 4-Nitrobenzanilide 183 Nitrobenzene 82, 204 4-Nitrobenzenediazonium 79 Nitrobenzoic acids 324 5(6)-Nitrobenzimidazole 292 4-Nitrobenzyl bromide 504 Nitro displacement 210 Nitrogen alkylation 380 4(5)-Nitroimidazole 292 2-Nitrophenol 180 4-Nitrophenyl cinnamate 505 1-Nitropropane 179 Nitrosobenzene 520 4-Nitrotoluene 384 Nonanomeric transformation 245 Nonstoichiometric hydrogen-bonded

complex 510 Non-symmetric quaternary ammonium

salts 486 Norbornadiene (NBD) 501 Norcarane 377 Normal Phase Transfer Catalysis 36

558

Nougier 245 Nucleophilic agents 135 Nucleophilic effects 86 Nucleophilic reactivity 4 Nucleophilicity 3 Nucleosides 265

O-alkylation 18, 379 O-allyldithiocarbonates 280 O-aryl glycosides 261 4,6, O-benzy lidene-2,3- O-ethylene-a-D-

glucopuranoside 252 o-bromostyrene 5\3 o-chloronitrobenzene 532 o-dichlorobenzene 203, 205 O'Donnell 303-6, 465, 477 O-glycosides 261 o-hydroxyacetophenone 279 o-nitrochlorobenzene 180 2-0-Nitrophenyl)-2-phenylbutyronitrile

148 o-nitrophenetole 180 O-(4-quinolinyl)phosphorothioates 295 2'-O-tosyladenosine 268 O-tritylations 250 Octacrbonyldicobalt 355 Ohkubo 524 Okawara 482 Oleic acid 417, 517 Oligomerization 349 Oligosaccharides 260, 262 Omega phase 6, 8, 61 Organic solvent 16 Organophilicity 16 Organophosphazene 49 Ortho-bromination of anilines 534 1,3-0xazine-2,4-diones 287 1,3-0xazine-2,4(3H)-dione 290 Oxaziridines 284, 328 2-0xazolidone 288 Oxazol-2-ones 287 Oxidation of benzyl chloride 518 Oxidation of cyclohexane 517 Oxidation of nitrogen compounds 327 Oxidation of 1-phenylethano1 521 Oxidation of sulfides to sulfoxides or

sulfones 521 Oxidation of sulfur compounds 238 Oxidative carboxylation 326 Oxidative decarboxylation 178 Oximation 190 Oxone 114, 284 4-0xyantipyrine 295 2-(4-0xy)benzoyl-3-phenyl-2,5-NBD 501 4,4'-Oxybiphenyldithiol 229 Oxybromination 179 Oxychlorination of olefins 519 4,4'-Oxydiphenyl sulfonyl chloride 230

INDEX

Oxyhalogenation of arenes 519 Oxyphenbutazole 179

p-bis(l-hydroxyethyl)benzene 223 p-bromostyrene 513 p-hydroxybenzoic acid 417 p-nitroanisole 28 p-nitrobenzoic acid 172 p-nitrochlorobenzene 180, 181 p-nitrophenetole 180 p-nitrotoluene 172, 192 Paczkowski 498, Palmitic acid 409, 417 Para-bromination of anilines 533 Particle diffusion 97 Pd-catalyzed telomerization of butadiene

537 PEG 73, 75, 76, 77,172, 185,187,189,

190, 193 PEG-400 Pelargonic acid 517 Pellicular resins 452 Pellicular sulfoxide resins 452 Pendant chalcone group 498 Pendant 4'-cyano-4-oxo biphenyl

mesogenic groups 502 Pendant haloalkyl groups 481 Pendant photosensitizing groups 501 Pendant vinyl ether groups 497 Pentachlorophenol 412 Pentaerythritol 245 Pentafluorobenzyl bromide (PFB-Br) 406 Pentillii 408 Pentofuranoside-3,5-diols 248 Peracetylated-rhamnosyl bromide 262 Perborate 321 Perbromocyclopentadiene 516 Percarbonate 321 Perfluoroalkyalkenes 373 Perfluoroalkyl iodides 373 Perfluorobenzene 229 Perhydropiperazine 292 Periodate 321 Periodate cleavage of 1,2-diol 254 Periodic acid 320 Peroxidized polypropylene 452 Peroxyoxalate chemiluminescence

detection 412 Persulfate 321 Phemylacetonitrile 149 Pheniramine 178 Phenol ethers 37 Phenolic steroids 412 Phenolphthalein 226 Phenothiazine 174, 289 Phenoxide anion 75 Phenoxy herbicides 408 Phenylacetetonitrile 173

INDEX 559

Phenylacetic acid 138, 170, 171 Phenylacetonitrile 138, 236, 444, 451 fJ-Phenylalanine 170 2-Phenylcycloalkanones 471 I-Phenylcylcopropanecarboonitrile 140 1,4-Phenylenediacetyl dichloride 217 I ,4-Phenylene( oxyacetyl)dichloride 217 Phenylhydrazones 142 2-Phenylindanone enol ate 304 3-Phenyl-2,5-NBD-2-carboxylate 501, 502 5-Phenyloxypyrazoles 295 Phenylphosphonic acid dichloride 238, 239 3-Phenylpropyl bromide 269 cc-Phenyl-cc-(2-pyridyl)acetonitriles 295 Phenylthioacetate 471 Phenyltriethylammonium chloride

(PTEAC) 196,498 2-Phenyl-2-vinylbutyronitrile 146 Phosgene 195,219,223,234 Phosphazene substitution 54 Phosphonium perbromides 534 Phosphonium salts 67, 93, 124 Phosphonium ylides 144, 339 Photochemical reactivity 502 Photocurable polyesters 500 Photoisomerization 502 Photooxidation catalyst 322 Photosensitive polymers 482, 498 Phthalimide 288, 303, 483 (-)-Physostigmine 464 Piperazines 174 Piperidinium salts 125 3-Piperidyloxo-2,5-NBD-2-carboxylate

502 Platinum colloid 527 Polarizability 19 Poly(acrylic acid) 504 Poly(amino acids) 455 Poly(arylenevinylene) 237 Poly(bischloromethyl oxetane) (PBCMO)

482 Poly(butyl acrylate) 238 Poly(2-chloroethyl acrylate) (PCEA) 481 Poly(2-chloroethyl methacrylate)

(PCEMA) 481 Poly[(chloromethyl)styrene] (PCMS) 481 Poly[2-(2-chloro-5-nitrobenzoyloxy)ethyl

methacrylate] 494 Poly[2-(4-chloro-3-nitrobenzoyloxy)ethyl­

methacrylate] 494 Poly(2-chloroethyl vinyl ether) (PCEVE)

481 Poly(2,6-dimethyl-I,4-phenylene oxide)

210 Poly(epiiodohydrin) 483 Poly(ester carbonates) 224 Poly(ether ketones) 208, 209 Poly(ethylene)glycols 205

Poly(glycidyl cinnamate) 482 Poly(ketone thioether) 230 Poly(L-alanine) 455 Poly(L-leucine) 456 Poly(methacrylic acid) (PMAA) 504 Poly(3-methyl-3-oxetanyl)methyl

methacrylate (PM OM) 505 Poly(4-methylstyrene) 516 Poly(nitro-2,4-phenyloxyundecyloxy) 211 Poly(oxovinyl thioether) 230 Poly(p-phenylene thioether) 228 Poly(vinyl azide) 482 Poly(vinyl chloride) (PVC) 481,514 Poly(vinyl chloroacetate) (PVCA) 481 Poly(vinyl dialkyldithiocarbamate) 482 Poly(vinyl ether)s 502 Polyacetylene layer 514 Poly bromide salts 533 Polycarbonates 30, 184,219 Polycarbonate-siloxane block copolymers

235 Polydithiocarbonates 227 Polyepichlorohydrin (PECR) 481 Polyesters 211 Polyetherification reactions 205, 207, 210 Polyethers 201 Polyethylene glycol 400, 249 Poly halide complexes 533 Poly hydrides 342 Polyhydroxyethers 204 Polymer-supported chiral catalysts 455 Polymer-supported imidazoles 300 Polymer-supported phenylarsonic acid 454 Polymer-supported poly(ethylene glycol)

(PEG) 437 Polymer-supported sulfoxide 451 Polymer supports 94 Polymer synthesis 200 Polymeric ion-exchange resins 116 Polymeric photosensitizers 482, 499 Polymers with pendant cyclic ether groups

504 Polyol alkylation 245 Polyoxapolyazaheterophanes 30 I Polyphosphonates 238 Polypropylene beads 452 Polystyren-bound quaternary salts 94 Polysulfonates 228 Polysulfones 228 Polythiocarbonates 224 Polythioesters 218 Polythioethers 228 Polythylene glycols 169 Polytrifluoroethoxycyclotriphosphazene 95 Polytrithiocarbonates 228 Polyvinylpyrrolidone 526 Porous catalysts 93 Positive-type photoresists 499

560 INDEX

Post-polymerization 451 Potapov 282 Potassium acetate 483, 484 Potassium azide 483, 484 Potassium benzoate 484 Potassium 4-benzoylphenoxide 501 Potassium carbazole 482 Potassium carbonate 209, 222, 223 Potassium chloride 115 Potassium cinnamate 499 Potassium crotonate 499 Potassium cyanate 503 Potassium dialkyldithiocarbamate 482 Potassium fluoride 114,415,531 Potassium hydroxide 115 Potassium iodide 483 Potassium 4-(N,N-dimethylamino)-

cinnamate 498 Potassium 4-nitro-l-naphthoxide 498 Potassium 4-nitrophenoxide 483, 498 Potassium permanganate 318, 384, 385 Potassium peroxodisulfate 238 Potassium persulfate 238 Potassium phenoxide 482, 484 Potassium phthalimide 476, 484 Potassium tert-butoxide 471 Potassium thioacetate 484 Potassium thiocyanate 122, 483, 484 Potassium thiophenoxide 483, 484 Potassium tribromophenoxide 38 Powdered KOH 201 Powell 338 Preparation of triphase catalysis 424 Process reliability 168 Product distribution 71 Proline 476 Propargyl alcohols 364 Propargyl bromide 504 Properties of triphase catalysts 433 Propionaldehyde diethyl acetal 159 Protecting groups 245 (+)-Pseudoephedrine 476 Pseudo-first-order 56 Pseudo-steady-state hypothesis 47 PTC rate matrix 14 Purine 293 PVC 30 PVC elimination 514 Pyrazines 276 Pyrazinobis(benzimidazole) 276 Pyrazole 291 Pyrenebutyryl chloride 223 Pyridazine 297 2-Pyridinecarboxaldehyde triphenyl-

phosphorane 257 Pyridine I-oxide 80, 85 Pyridine N-oxide 308, 535 Pyridinium hydrobromide perbromide 534

Pyridinium salts 286, 299 Pyridofuroxane 285 2-Pyridones 287 Pyridoxine hydrochloride 177 Pyrimidine 267, 293, 297 Pyrrole 142, 287 4-Pyrrolidinipyridine 535 Pyrrolidinone 175 2-Pyrrolidone 301

Quadricyclane (QC) 501 Quaternary ammonium hydrates 511 Quaternary ammonium peroxometalate

520 Quaternary ammonium peroxotungsto-

phosphate catiyst 520 Quaternary ammonium perruthenate 327 Quinacridone 290 Quinazoline-2,3-dione 293 Quininium 304 Quinn 119, 191 Quinolines 287 Quinolphos 187 Quinoxalino[2,3-b][ I ,4]benzothiazines

289 Quinuclidinium 304 Quirk 118

Radical polymerization 238 Radioactive halides 182 Ranganekar 182, 183 Reactions of carbanions 137 Reactive catalyst 56 Reactivity of anions 4, 5 Reed 184 Reetz 118, 527 Regen 93, 424 Regioselective monobenzoylation 249 Reimer-Tiemann reaction 194 Reissert compounds 294, 375 Reverse Menschuttkin reaction 123, 124 Reverse phase transfer catalysis 79 RhCIJ-Aliquat 336 complex 347, 349 Rhodanine 294 RhOne Poulenc 537 Ring substitution 94, 98, 432 Robinson annelations 464, 302 Roeske 483 Rokicki 215 Role of water 6 Roovers 483 Ruhrchemie 537 Ruthenium tetraoxide 253

S-alkylthioacridines 296 S-anions 488 S-electrophiles 149 S-glycosides 263

INDEX 561

(S)-N,N-dialkyl-2-(hydroxydiaryl-methyl)pyrrolidinium halides 304

Saccharin 288 Saigo 302 Salcomine 177, 327 Sasson 7,11,172,179,194,328,384,511 Scanning tunnelling microscopy (STM)

527 Schacht 483 Schlott 225 Schotten-Baumann esterificaiton of tert-

butanol 529 Schwesinger 125 Sebacoy1 dichloride 214 Selectivity coefficient 3, 9, 113 Semenov 520 Sepulveda 120 Shaffer 536 Sharma 185, 195 Shimada 415 Shin 417 Sialic acid 255 Sialic acid glycosides 262 Silica gel 93, 195 Silica gel-supported phosphonium salt 447 Silylation 251 Simmons-Smith cyclopropanation 257 Simplified dynamic model 47 Single electron transfer 210 Sirovskii 16 Sjoeberg 119 Sodium acetate 81, 484 Sodium azide 118, 298,484 Sodium benzoate 484 Sodium cyanide 93, 483 Sodium diethyl malonate 483 Sodium dimethyldithiocarbamate 483 Sodium dithionite 171 Sodium 4-dodecylbenzenesulfonate 79 Sodium dodecylsulfonate 420 Sodium ethyl cyanomalonate 483 Sodium ethyl xanthate 121 Sodium iodide 246 Sodium malononitrile 483 Sodium molybdate 520 Sodium N,N-diethyldithocarbamate 484 Sodium nitrite 127, 179 Sodium periodate 253 Sodium phenoxide 73 Sodium sulfide 171,536 Sodium thiocyanate 122, 484 Sokolov 523 Sol-gel encapsulated Co-ammonium ion

pairs 351 Sol-gel encapsulated Pt-ammonium ion

pairs 351 Sol-gel encapsulated Rh-ammonium ion

pairs 351

Solar energy storage-exchange systems 501

Solid-liquid anion exchange 115 Solid-liquid systems 3 Solid-liquid-solid conditions 269 Solid-solid phase transfer catalysis 95 Solid-solid-liquid systems 25 Sololov 518 Solubility ratio 116 Solvation 9, 54 Solvent effect 484, 490 Sonochemical reactivity 370 Sonochemical switching 371, 383 Sonochemistry 369 Spacer-chain effect 445 ( - )-sparteine 304 Specific conductance 74 Spiperone 292 Spray drying 127 Stability of triphase catalysts 453 Stable bimetallic Pd-Pt colloid 527 Stable nanostructured metal colloids 526 Stagnant film model 95 Starks 7, 9, 29, 31, 37, 111 Stearic acid 417 Stearyl stearate 391 Stepwise hydrogenation 347 Stereoselective dichlorocarbene addition

257 Sterically hindered amines 112 Sterically hindered pendant chloromethyl

groups 494 Stilbene 67 Stirring conditions 430 Structure of triphase catalysts 433 Structure-activity relationship 15 Styrene oxide 358 Suberonitrile 185 Substituted stilbenes 182 Succinic acid 215 Succinimide 142, 288 Sulfolane 440 Sulfonium 144 Sulfonium ylides 286 Sulfonoxycarbamate 378 Sulfonyl fluorides 21 Sulphide 408 4,4' -Sulphonyldiphenol 240 Sumitomo 113 Supported crown ethers 437 Supported macrocyclic polyethers 443 Supported tetraphenylphosphonium salt

453 Surface tension 14 Surface treatment of solid PVC 514 Swelling power 94, 100 Swelling ratio 433 Synthesis of anhydrides 345

562 INDEX

Synthetic pyrethroid 375 Szeja 245

Takeishi 483, 536 Tamura 514 Tanimoto 482 TEBA 283 Telford 430 Temephod 187 Temperature stable PTe 123 Terephthalic acid dichloride 212 Terephthalic 211 Tereschenko 284 Ternary complexes 12 tert-Butyl cyanoacetate 236 tert-Butyl hydroperoxide 523 tert-Butyl isocyanide 154 I-tert-Butylperoxy)tetralin 523 4-tert-Butylpyridine 322 Tetraacetylmannose-2-triflate 356 Tetraalkylammonium fluorides 116 Tetraalkylammonium hydroxides 118 3,3'5,5' -Tetrabromobisphenol 233 Tetrabromopyridine 281 Tetrabutylammonium 9-methylfluorenide

118 Tetrabutylammonium bifluoride 120 Tetrabutylammonium bromide 189,201,

202, 246, 513 Tetrabutylammonium chloride (TBAC)

128 225, 483, 486 Tetrabutylammonium diethylmalonate 118 Tetrabutylammoniurn difluorotriphenyl­

stannate 120 Tetrabutylammoniurn dihydrogen­

trifluoride 514 Tetrabutylammonium fluoride 118, 514 Tetrabutylammoniurn hydrogensulfate

210, 245, 291 Tetrabutylammoni urn hydrogensulpha te

(TBAS) 483 Tetrabutylammoniurn hydrogen sulfide

227 Tetrabutylammoniurn hydroxide (TBAH)

483 Tetrabutylammoniurn iodide (TBAI) 486 Tetrabutylammonium perchlorate (TBAP)

486 Tetrabutylphosphonium bromide (TBPB)

202,486 Tetrachloroaziridines 284 Tetrachloroterphthalic acid dichloride

212 Tetracyanoquinodimethane 375 Tetraethylammonium acetate tetrahydrate

192,511 Tetraethylammonium bromide (TEAB)

246,485

Tetraethylammonium chloride 483, 528, 533

Tetraethylammonium fluoride 512 Tetrafluoroisophthalic acid dichloride 213 Tetrafluoroisophthalonitrile 210 Tetrahexylammonium bromide (THAB)

234, 485, 514, 524 Tetrahexylammonium formate 128 Tetrahexylammonium hydrogensulfate 408 Tetrahydropyrazinones 277 Tetrahydrothiophene 484 Tetrakis(cetylpyridinium)decatungstate

321 Tetralone 467 2-Tetralone 471 Tetramethylammonium bromide (TMAB)

485 Tetramethylammonium carbonate 119 Tetramethylammonium chloride 528 Tetramethylammonium fluoride

tetrahydrate 192, 511 Tetramethylammonium hydroxide 118 Tetramethylammonium propionate 119 Tetramethylethylenediamine 191 Tetramethylurea 440 Tetra-n-butylammonium acetate 118 Tetra-n-butylammonium azide 118 Tetra-n-butylammonium bibenzoate 130 Tetra-n-butylammonium bromide III Tetra-n-butylammonium chloride 123, 512 Tetra-n-butylammonium hydrogensulfate

203, 204, 205 Tetra-n-butylammonium hydroxide 129 Tetra-n-heptylammonium chloride 512 Tetra-n-octylammonium hydroxide 129 2,3,4,6-Tetra-O-benzyl-cx-D-

glucopyranosyl bromide 261 2,3,4,6-Tetra-O-benzyl-D-glucose 262 Tetraoctadecylammonium bromide 527 Tetraoctylammonium bromide (TOAB)

485 Tetraoctylammonium fluoride 114, 511 Tetrapentylammonium bromide (TPEAB)

485 Tetraphenylphosphonium chloride 127 Tetraphenylphosphonium hydrogen

difluoride 468 Tetrapropylammonium bromide (TPAB)

485 Tetrazoles 293, 294 Tetrazolium salts 286 Theophyline 293 Thiadiazepines 276 1,2,4-Thiadiazoles 286 Thiazoles 278 Thiele modulus 57, 101, 104 Thietane S,S-dioxides 277 Thiirans 357

Thin liquid film membrane 511 Thioacridone 296 Thioalkylating agents 149 Thiocyanate 22, 408 Thiocyanate anion 536 Thiodiazepines 278 Thionyl chloride 528 Thiophenetricarbonylchromium 379 Thiophosgene 225, 227, 235 Thiouracil 296 2-Thioxopyrimidine 296 Three-phase phase transfer catalytic

reactions 93 Thymine 293 Tomoi 93 Topo-induced stereoselectivity 298 Topology of PTe displacement 14 Toullee 119 Transacylations 307 Trans-I,4-dichlorobut-2-ene 204 Transfer hydrogenation 524 Trans-stilbene 71 Triarylformazans 300 Triaryl phosphates 185 Triazatrione 281 1,3,5-Triazine-2-thio-4,6-diones 287 1,3,5-Triazine-2,4,6-triones 287 1,3,5-Triazines 297 1,2,3-Triazoles 328 1,2,4-Triazoles 292, 293 Tribochemical effect 372 2,4,6-Tribromophenol 41, 103, 185, 533 Tributylamine 436 Tributylbenzylammonium cyanide 128 Tributylethylammonium bromide 497 Tributyl(hexadecyaal)phosphonium

bromide 264 Tributylhexadecylammonium bromide 512 Tributylmethylammonium chloride 128 Tributylmethyl phosphonium bromide 512 Tributylphosphine (TBP) 491 Tributylstannane 471 Tricaprylmethylammonium fluoride 128 Tricarprylmethylammonium chloride III 1,2,4-Trichlorobenzene 513 Trichloromethyl carbanion 150 Trichloromethyl chloroformate 234 Trichloropyridinol 187 3,5,6-Trichloropyridin-2-o1 192 Trichloropyridinolate 536 2,4,6-Trichloro-I ,3,5-triazine 301 Triethylbenzylammonium chloride III Triethylbenzylammonium chloride 444,

528 Triethylenetetramine 439 2,2,2-Trifbromophenol 95 2,2,2-Trifluoroethanol 49, 95 Triisobutylmethylammonium tosylate 125

INDEX 563

2,3,6-Trimethylhydroquinone 177 2,3,6-Trimethylphenol 177 Trioctylphosphine oxide (TOPO) 526 Triphase catalysis 16, 93, 96, 424 Triphase catalyst 94, 100 Triphenylantimony dichloride 240 Triphenylmethane 320 Triphenylphosphine trisulfonate (TPPS)

537 Triphenylphosphoranylidenemethyl 295 1,2,4-Triphenyltetrazolium salts 300 2,4,6-Triphospha-I,3,5-triazines 298 Triple dehydrochlorination 513 Tris[2-(2-methoxyethoxy)ethyl]amine

(TDA-I) 266, 267 Trist 114 Trithione 281 Triton B 147 Triton-X 100419 (+ )-tryptoquinone A 302 Tundo 447 Turbine stirrer 458 Two-film theory 43

Ullmann-like amine arylations 345 Ultrasonic agitation 172 Ultrasonic irradiation 201, 534 10-Undecanoic acid 419 a/.i-Unsaturated esters 344 Unsaturated hydroxyl act ones 363 Unsaturated keto acids 363 Uracil 287, 293 Uranium from sea water 503 Uridine 293

Valproic acid 420 Vanillin 396 Venturello 519 Vicarious substitution 27 Vilsmeier reagent 127 Vilsmeier salts 126 Vinyl acetate 145 Vinyl dibromides 354 a,/.i-Vinyl epoxides 357 4-Vinyl-I ,2-epoxycyclohexanes 365 Vinylidend chloride 184 Viscosity 201 Vitamin E 177 Volume ratio 43, 430

Wacker process 270 Wacker-type oxidation 323 Wamser 535 Wang 38, 54, 66, 75, 100, 346, 535 Wastewater treatment 196 Water 510 Water-insoluble free radical initiators 271 Water-soluble metal catalysts 536

564

Water-soluble vinyl monomers 271 Wei 189 Weissler reaction 373 Williamson ether synthesis 194, 58 Wittig reaction 67, 145, 194,254, 255,

278 Wittig-Horner reaction 145, 257 WOJ equilibrium reaction 85, 90 Wu 380 Wynberg 519

Xiang 180

INDEX

Yasaka417 Ylide complexes 339 Ylide-mediated reaction 67 Yu 303 Yuan 391, 392 Yuang 396

Zanthine 293 Zephiran chloride 170 Zhang 119 Zhdanov 257 Zoltewicz 125