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Electronic Supplimentary Information
Synthesis of Substituted Nitroolefins: A Copper Catalyzed
Nitrodecarboxylation of Unsaturated Carboxylic Acids
Balaji V. Rokade and Kandikere Ramaiah Prabhu*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka,
India.
Telephone: +91-80-22932887; Fax: +91-80-23600529
Contents: Page no.
1. General experimental E SI - 2
2. Preparation of starting materials ESI - 2
3. Typical experimental procedure and spectral data ESI 3-10
4. 1H and
13C NMR spectra ESI 11 – 58
5. Mass Spectra (EI-MS) of selected compounds ESI 59 - 67
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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ESI - 2
1. General experimental :
NMR spectra were recorded in CDCl3 using Tetramethylsilane (TMS; δ = 0.00 ppm) as internal
standards for 1H NMR and corresponding residual non-deuterated solvent signal (CDCl3: δ =
77.00 ppm) was used as internal standards for 13
C NMR. Mass spectra were measured with
Micromass Q-Tof (ESI-HRMS) and Shimadzu gas chromatograph mass spectrometer model QP-
2010 Ultra EI. Column chromatography were carried out on silica gel 230-400 mesh or 100-200
mesh (Merck). Chemicals obtained from commercial suppliers were used without further
purification.
2. Preparation of starting materials:
The starting materials, substituted cinnamic acid derivatives were prepared from the
corresponding aldehydes using general procedure shown in the following scheme and spectral
data are in agreement with the literature.
a) NaH (60% mineral oil, 2 equiv.), Triethylphosphonoacetate ( 1.5 equiv.) in THF at 0 °C to 60
°C. b) NaOH ( 5 equiv., EtOH:H2O in 8:2 ratio at 60 °C).
All compounds were analyzed by NMR, IR and MS spectroscopy and also compared with
known compounds.
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ESI - 3
Typical experimental procedure
α,β-Unsaturated acid (0.5 mmol), CuCl (0.05 mmol) and tertiary butyl nitrite (1.0 mmol) and
CH3CN (2 mL) were added in to an oven dried round bottom flask, the reaction mixture stirred at
80 °C for 12 -18 h and the completion of the reaction was monitored by thin layer
chromatography. After completion of reaction, the reaction mixture was cooled to room
temperature, and solvent was removed under reduced pressure to obtain the crude product, which
was purified on silica gel column to get pure product.
2-nitroethene-1,1-diyl)dibenzene (2a). Prepared as shown in general experimental procedure.
Yellow solid: Yield 96% (108 mg); mp 84-86 °C (lit.1 86-87 °C Rf (); 15% EtOAc/Hexane) 0.80;
IR (KBr, cm-1
) 1517, 1340; 1H NMR (400 MHz, CDCl3) 7.35-7.44 (m, 7H), 7.27 (d, J = 7.2
Hz, 2H), 7.20-7.26(m, 2H); 13
C NMR (100 MHz, CDCl3) 150.4, 138.0, 135.5, 132.3, 130.9,
129.3, 128.9, 128.8, 128.7, 128.4; MS (M/Z) 225 (M+).
(E)-(1-nitroprop-1-en-2-yl)benzene (2b). Prepared as shown in general experimental
procedure. Yellow liquid: Yield 71% (58 mg); Rf (15% EtOAc/Hexane) 0.75; IR (Neat, cm-1
)
1555, 1517, 1340, 1147; 1H NMR (400 MHz, CDCl3) 7.45(m, 5H), 7.31(s, 1H), 2.65(s, 3H);
13C NMR (100 MHz, CDCl3) 149.5, 138.2, 136.3, 130.3, 129.0, 126.8; MS (M/Z) 163 (M+).
(E)-1-methyl-4-(1-nitroprop-1-en-2-yl)benzene (2c). Prepared as shown in general
experimental procedure. Yellow liquid: Yield 70% (62 mg); Rf (10% EtOAc/Hexane) 0.70; IR
(Neat, cm-1
) 2924, 1607, 1336, 1018; 1H NMR (400 MHz, CDCl3) 7.36 (d, J = 8 Hz, 2H), 7.32
(s, 1H), 7.24 (d, J = 8 Hz, 2H), 2.63 (s, 3H), 2.39 (s, 3H); 13
C NMR (100 MHz, CDCl3) 150.0,
140.9, 135.7, 135.3, 129.7, 126.7, 21.2, 18.4; HRESI-MS (M/Z) Calculated for C1oH11NO2
(M+Na) 200.0687, found (M+Na) 200.0685.
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(E)-1-methoxy-4-(1-nitroprop-1-en-2-yl)benzene (2d). Prepared as shown in general
experimental procedure. Yellow liquid: Yield 52% (50 mg); Rf (15% EtOAc/Hexane) 0.75; IR
(Neat, cm-1
) 2932, 1600, 1513, 1333, 1249, 1019; 1H NMR (400 MHz, CDCl3) 7.44 (d, J = 8
Hz, 2H), 7.34 (s, 1H), 6.95(d, J = 8 Hz, 2H), 3.86 (s, 3H), 2.64 (s, 3H); 13
C NMR (100 MHz,
CDCl3) 161.6, 149.7, 135.1, 130.2, 128.4, 114.4, 55.4, 18.3; HRESI-MS (M/Z) Calculated for
C10H11NO3 (M+Na) 216.0637, found (M+Na) 216.0637.
(E)-1-bromo-4-(1-nitroprop-1-en-2-yl)benzene (2e). Prepared as shown in general
experimental procedure. Yellow liquid: Yield 54% (66 mg); Rf (15% EtOAc/Hexane) 0.80; IR
(Neat, cm-1
) 1516, 1339; 1H NMR (400 MHz, CDCl3) 7.58 (d, J = 8 Hz, 2H), 7.32 (d. J = 8 Hz,
2H), 7.28 (s, 1H), 2.62 (s, 3H); 13
C NMR (100 MHz, CDCl3) 148.5, 137.1, 136.4, 136.3, 128.3,
124.9, 18.4; HRESI-MS (M/Z) Calculated for C9H8BrNO2 (M+) 240.9738, found (M+)
240.9740.
(E)-2-(1-nitroprop-1-en-2-yl)naphthalene (2f). Prepared as shown in general experimental
procedure. Yellow liquid: Yield 70% (75 mg); Rf (15% EtOAc/Hexane) 0.80; IR (Neat, cm-1
)
2926, 1616, 1333, 1018; 1H NMR (400 MHz, CDCl3) 7.95 (s, 1H), 7.90 - 7.87 (m, 3H), 7.57 -
7.50 (m, 3H), 7.45 (s, 1H), 2.75 (s, 3H); 13
C NMR (100 MHz, CDCl3) 149.9, 136.6, 135.4,
134.0, 133.2, 128.9, 128.6, 127.8, 127.7, 127.5, 127.0, 123.7, 18.6; HRESI-MS (M/Z) Calculated
for C13H11NO2 (M+Na) 236.0687, found (M+Na) 236.0691.
(E)-2-(1-nitroprop-1-en-2-yl)thiophene (2g). Prepared as shown in general experimental
procedure. Yellow liquid: Yield 55% (47 mg); Rf (15% EtOAc/Hexane) 0.75; IR (Neat, cm-1
)
2926, 2103, 1638, 1248, 1018; 1H NMR (400 MHz, CDCl3) 7.57 (d, J = 4 Hz, 1H), 7.47-7.50
(m, 2H), 7.13-7.15 (m, 1H), 2.71 (s, 3H); 13
C NMR (100 MHz, CDCl3) 142.9, 140.5, 133.7,
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129.6, 129.2, 128.6, 17.8; HRESI-MS (M/Z) Calculated for C7H7NO2S (M+Na) 192.0095, found
(M+Na) 192.0099.
2-(3-nitroprop-1-en-2-yl)pyridine (2ha) and (E)-2-(1-nitroprop-1-en-2-yl)pyridine (2hb).
Prepared as shown in general experimental procedure. Yellow liquid: Yield 52% (66 mg); Rf
(15% EtOAc/Hexane) 0.50; IR (Neat, cm-1
) 2923, 1554, 1344, 1018; 1H NMR (400 MHz,
CDCl3) 2ja 8.53 (d, 1H), 7.73-7.65 (m, 2H), 7.23-7.20 (m, 1H), 6.17 (s, 1H), 5.72 (s, 1H), 5.55
(s, 2H); 2jb 8.68 (d, 1H), 7.81 (s, 1H), 7.79-7.77 (m, 1H), 7.57 (d. J = 8 Hz, 1H), 7.38-7.34 (m,
1H), 2.66 (s, 3H); 13
C NMR (100 MHz, CDCl3) 2ja and 2jb 154.6, 154.5, 149.8, 149.0, 146.2,
138.6, 138.2, 137.1, 136.6, 124.7, 123.0, 122.5, 121.8, 119.7, 77.4, 15.8; HRESI-MS (M/Z)
Calculated for C8H8N2O2 (M+H) 165.0664, found (M+H) 165.0659.
(E)-1-methoxy-4-(2-nitrovinyl)benzene (3a). Prepared as shown in general experimental
procedure. Yellow solid: Yield 92% (82 mg); mp 85-86 °C (lit.2 84-86 °C); Rf (10%
EtOAc/Hexane) 0.70; IR (KBr, cm-1
) 2931, 1603, 1338, 1255, 1173, 1025; 1H NMR (400 MHz,
CDCl3) 7.97 (d, J = 12 Hz, 1H), 7.53 (d, J = 12 Hz, 1H), 7.51 (d, J = 8Hz, 2H), 6.96 (d, J = 8
Hz, 2H), 3.87(s, 3H); 13
C NMR (100 MHz, CDCl3) 162.9, 139.0, 135.0, 131.1, 122.5, 114.9,
55.5; HRESI-MS (M/Z) Calculated for C9H9NO3Na (M+Na) 202.0480, found (M+Na) 202.0481.
(E)-(2-nitrovinyl)benzene (3b). Prepared as shown in general experimental procedure. Yellow
solid: Yield 82% (61 mg); mp 55-58 °C (lit.2 56-60 °C); Rf (15% EtOAc/Hexane) 0.8; IR (KBr,
cm-1
) 2829, 1632, 1513, 1347; 1H NMR (400 MHz, CDCl3) 7.99 (d, J = 13.6 Hz, 1H), 7.43-
7.60 (m, 6H); 13
C NMR (100 MHz, CDCl3) 139.0, 137.0, 132.1, 130.0, 129.3, 129.1; MS
(M/Z): 149 (M+).
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(E)-1-methyl-4-(2-nitrovinyl)benzene (3c). Prepared as shown in general experimental
procedure. Yellow solid: Yield 52% (42 mg); mp 101-103 °C (lit.3 103 °C); Rf (15%
EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 1632, 1497, 1341; 1H NMR (400 MHz, CDCl3) 7.98 (d, J
= 13.6 Hz, 1H), 7.56 (d, J = 13.6 Hz, 1H), 7.42 (d, J = 8 Hz, 2H), 7.25 (d, J = 10 Hz, 2H), 2.48
(s, 3H); 13
C NMR (100 MHz, CDCl3) 143.0, 139.1, 136.3, 130.1, 129.2, 127.3; HRESI-MS
(M/Z) Calculated for C9H9NO2 (M+Na): 186.0531, found (M+Na): 186.0533.
(E)-1-(2-nitrovinyl)naphthalene (3d). Yellow solid: Yield 91% (91 mg); mp 84-86 °C (lit.3 84
°C); Rf (15% EtOAc/Hexane) 0.8; Prepared as shown in general experimental procedure. IR
(KBr, cm-1
): 1515, 1505, 1342, 1018; 1H NMR (400 MHz, CDCl3) 8.82 (d, J = 13.2 Hz, 1H),
8.13 (d, J = 8.4Hz, 1H), 8.0 (d, J = 8.4 Hz, 1H), 7.92 (d, J = 8 Hz, 1H), 7.74 (d, J = 6.8 Hz,
1H), 7.57-7.66 (m, 3H), 7.50-7.54 (t, J = 7.6 Hz, J = 15.2 Hz, 1H); 13
C NMR (100 MHz, CDCl3)
138.4, 136.1, 133.8, 132.5, 131.5, 129.0, 127.7,127.0, 126.8,126.3, 125.4, 123.0; MS (M/Z)
199 (M+).
(E)-1,2-dimethoxy-4-(2-nitrovinyl)benzene (3e). Prepared as shown in general experimental
procedure. Yellow solid: Yield 69% (72 mg); mp 134-136 °C (lit.4 137 - 140 °C); Rf (15%
EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 1599, 1490, 1343, 1272; 1H NMR (400 MHz, CDCl3) 7.96
(d, J = 13.6 Hz, 1H), 7.54(d, J = 13.6 Hz, 1H), 7.17(d, J = 8 Hz, 1H), 7.01(d, J = 1.2 Hz, 1H),
6.92 (d, J = 8 Hz, 1H), 3.94(s, 3H), 3.93(s, 3H); 13
C NMR (100 MHz, CDCl3) 152.8, 149.5,
139.3, 135.1, 124.6, 122.7, 111.3, 110.2, 56.0, 55.9; HRESI-MS (M/Z) Calculated for
C10H11NO4 (M+Na) 232.0586, found (M+Na) 232.0585.
(E)-1-(benzyloxy)-4-(2-nitrovinyl)benzene (3f). Prepared as shown in general experimental
procedure. Yellow solid: Yield 60% (77 mg); mp 120-122 °C (lit.5 121-122 °C); Rf (15%
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EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 1601, 1491, 1344, 1248; 1H NMR (400 MHz, CDCl3) 7.96
(d, J = 16 Hz, 1H), 7.48-7.52 (m, 3H), 7.35-7.42 (m, 5H), 7.02 (d, J = 8Hz, 2H), 5.12 (s, 2H);
13C NMR (100 MHz, CDCl3) 162.0, 138.9, 135.6, 135.1, 131.1, 128.7, 128.3, 127.4, 122.7,
70.2; HRESI-MS (M/Z) Calculated for C15H13NO3 (M+Na) 278.0793, found (M+Na) 278.0792.
(E)-1-(2-nitrovinyl)-3-phenoxybenzene (3g). Prepared as shown in general experimental
procedure. Yellow solid: Yield 84% (101 mg) and 45% (54 mg); mp 58-59 °C (lit.6 57-59 °C); Rf
(15% EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 1579, 1519, 1487, 1344, 1230; 1H NMR (400 MHz,
CDCl3) 7.95 (d, J = 14 Hz, 1H), 7.53 (d, J = 14Hz, 1H), 7.38-7.44 (m, 3H), 7.28 (d, J = 7.2Hz,
1H), 7.18-7.21 (t, J = 7.2 Hz, J = 14.8 Hz, 1H), 7.06-7.15 (m, 2H), 7.05 (d, J = 7.6 Hz, 2H); 13
C
NMR (100 MHz, CDCl3) 158.3, 156.1, 138.4, 137.6, 131.7, 130.7, 130.0, 124.2, 123.8, 122.0,
119.4, 118.2; HRESI-MS (M/Z) Calculated for C14H11NO3 (M+H) 242.0817, found (M+H)
242.0819.
(E)-1-(2-nitrovinyl)-4-(trifluoromethyl)benzene (3h). Prepared as shown in general
experimental procedure. Yellow solid: Yield 46% (50 mg) and 38% (41 mg); mp 93-94 °C (lit.2
92-95 °C); Rf (15% EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 2926, 2102, 1636, 1324, 1263, 1019; 1H
NMR (400 MHz, CDCl3) 8.03 (d, J = 12 Hz, 1H), 7.73 (d, J = 8 Hz, 2H), 7.68 (d, J = 8 Hz,
2H), 7.62 (d, J = 12 Hz, 1H); 13
C NMR (100 MHz, CDCl3) 138.9, 137.1, 133.5, 133.4 (q, J =
32.7 Hz), 129.2, 126.4, 123.5 (q, J = 271 Hz); MS (M/Z) 217 (M+).
(E)-4-(2-nitrovinyl)benzonitrile (3i). Prepared as shown in general experimental procedure.
Yellow solid: Yield 36% (31 mg) and 32% (28 mg); mp 183-185 °C (lit.7 180-186 °C) Rf (15%
EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 2227, 2102, 1638, 1348; 1H NMR (400 MHz, CDCl3) 7.99
(d, J = 12 Hz, 1H), 7.76(d, J = 8 Hz, 2H), 7.63-7.68 (t, J = 8 Hz, J = 20 Hz, 2H) , 7.60 (s, 1H);
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13C NMR (100 MHz, CDCl3) 139.4, 136.5, 134.3, 133.0, 129.3, 117.8, 115.2; MS (M/Z) 174
(M+).
(E)-1-bromo-2-(2-nitrovinyl)benzene (3j). Prepared as shown in general experimental
procedure. Yellow solid: Yield 45% (52 mg); mp 84-87 °C (lit.8 82-87 °C); Rf (15%
EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 1635, 1522, 1340, 1018; 1H NMR (400 MHz, CDCl3) 8.39
(d, J = 16 Hz, 1H), 7.69 (d, J = 4Hz, 1H), 7.55-7.68 (m, 1H), 7.52 (s, 1H), 7.32-7.41 (m, 2H);
13C NMR (100 MHz, CDCl3) 138.8, 137.6, 134.0, 133.0, 130.3, 128.4, 128.0, 126.3; MS (M/Z)
229 (M+).
(E)-1-fluoro-2-(2-nitrovinyl)benzene (3k). Prepared as shown in general experimental
procedure. Yellow solid: Yield 68% (57 mg); mp 44-46 °C; Rf (15% EtOAc/Hexane) 0.8; IR
(KBr, cm-1
) 1635, 1509, 1357, 1216; 1H NMR (400 MHz, CDCl3) 8.05 (d, J = 13.6 Hz, 1H),
7.73 (d, J = 14Hz, 1H), 7.46-7.54 (m, 2H), 7.16-7.26 (m, 2H); 13
C NMR (100 MHz, CDCl3)
163.1, 160.6, 139.4, 139.2, 133.7, 133.6, 132.4, 131.4, 131.3, 125.0, 124.9, 118.5, 118.3, 116.7,
116.5; HRESI-MS (M/Z) Calculated for C8H6FNO2 (M+Na) 190.0280, found (M+Na) 190.0305.
(E)-1-chloro-4-(2-nitrovinyl)benzene (3l). Prepared as shown in general experimental
procedure. Light yellow solid: Yield 50% (46 mg); mp 110-111 °C (lit.9 110-111 °C); Rf (15%
EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 1635, 1491, 1340; 1H NMR (400 MHz, CDCl3) 7.97 (d, J
= 12 Hz, 1H), 7.57 (d, J = 12 Hz, 1H), 7.50 (d, J = 8 Hz, 2H), 7.44 (d, J = 8 Hz, 2H); 13
C NMR
(100 MHz, CDCl3) 138.3, 137.7, 137.4, 130.2, 129.7, 128.5; MS (M/Z) 183 (M+).
(E)-2-(2-nitrovinyl)thiophene (3m). Prepared as shown in general experimental procedure.
Yellow solid: Yield 72% (56 mg); mp 81-83 °C (lit.2 80-82 °C); Rf (15% EtOAc/Hexane) 0.8; IR
(KBr, cm-1
): 2102, 1635, 1325, 1265; 1H NMR (400 MHz, CDCl3) 8.15 (d, J = 12 Hz, 1H),
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7.57 (d, J = 8 Hz, 1H), 7.46-7.50 (m, 2H), 7.14-7.16 (t, J = 4 Hz, J = 8 Hz, 1H); 13
C NMR (100
MHz, CDCl3) 135.3, 134.6, 133.7, 132.1, 131.6, 128.8; HRESI-MS (M/Z) Calculated for
C6H5NO2S (M+Na) 177.9939, found (M+Na) 177.9938.
(E)-2-(2-nitrovinyl)furan (3n). Prepared as shown in general experimental procedure. Yellow
solid: Yield 41% (28.5 mg); mp 67-69 °C (lit.10
68-70 °C); Rf (15% EtOAc/Hexane) 0.8; IR
(KBr, cm-1
): 1631, 1499, 1325, 1018; 1H NMR (400 MHz, CDCl3) 7.78 (d, J = 13.2 Hz, 1H),
7.59 (d, J = 0.4 Hz, 1H), 7.52 (d, J = 13.6 Hz, 1H), 6.89 (d, J = 3.2 Hz, 1H), 6.57-6.58 (m, 1H);
13C NMR (100 MHz, CDCl3) 146.8, 146.6, 135.0, 125.4, 120.0, 113.3; MS (M/Z) 139 (M+).
(E)-(2-(2-nitrovinyl)-1H-indol-1-yl)(phenyl)methanone (3o). Prepared as shown in general
experimental procedure. Yellow solid: Yield 75% (109 mg); mp 42-45 °C; Rf (15%
EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 1607, 1438, 1261, 1019; 1
H NMR (400 MHz, CDCl3) 8.05
(d, J = 12 Hz, 1H), 7.77-7.75 (m, 2H), 7.72-7.64 (m, 2H), 7.56-7.50 (m, 3H), 7.28-7.21 (m, 3H),
7.14 (d, J = 8 Hz, 1H)13
C NMR (100 MHz, CDCl3) 168.9, 138.9, 136.5, 134.2, 134.0, 131.2,
130.1, 129.5, 129.1, 128.3, 126.6, 123.9, 122.0, 114.7, 113.8; HRESI-MS (M/Z) Calculated for
C17H12N2O3 (M+Na) 315.0746, found (M+Na) 315.0746.
((1E,3E)-4-nitrobuta-1,3-dien-1-yl)benzene (3p). Prepared as shown in general experimental
procedure. Yellow solid: Yield 34% (30 mg); mp 45-47 °C (lit.11
45-47 C); Rf (15%
EtOAc/Hexane) 0.8; IR (KBr, cm-1
) 2922, 1622, 1433, 1018; 1H NMR (400 MHz, CDCl3)
7.73-7.79 (t, J = 12 Hz, J = 24.4 Hz, 1H), 7.49-7.51 (t, J = 2.8 Hz, J = 7.6 Hz, 2H), 7.38-7.40 (m,
3H), 7.22 (d, J = 13.2 Hz, 1H), 7.13 (d, J = 15.6 Hz, 1H), 6.82-6.88 (dd, J = 11.6 Hz, J = 15.2
Hz, 1H); 13
C NMR (100 MHz, CDCl3) 146.0, 139.1, 138.6, 135.0, 130.3, 129.0, 127.7, 120.5;
MS (M/Z) 175 (M+).
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Refereneces
1 T. H. H. Hsieh and V. M. Dong, Tetrahedron 2009, 65, 3062.
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5 W. E. Parham, C. Jr. Serres and P. R. O'Connor, J. Am. Chem. Soc. 1958, 80, 588.
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7 M. A. Brook and D. Seebach, Can. J. Chem. 1987, 65, 836.
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10 D. H. O'Donovan and I. Rozas, Tetrahedron Lett. 2012, 53, 4532.
11 M. Tsakos and C. G. Kokotos, Eur. J. Org. Chem. 2012, 576.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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ESI - 11
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
0
7.2
0
7.2
1
7.2
2
7.2
3
7.2
6
7.2
7
7.2
8
7.3
5
7.3
7
7.3
7
7.3
9
7.4
1
7.4
2
7.4
2
7.4
3
7.4
3
7.4
5
2.0
0
2.1
0
7.1
5
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ESI - 12
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
82
77.0
00
77.3
18
128
.440
128
.739
128
.826
128
.854
129
.256
130
.851
134
.339
135
.478
137
.019
150
.417
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 13
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 14
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 15
10 9 8 7 6 5 4 3 2 1 0 ppm
0.0
0
2.4
0
2.6
3
7.2
3
7.2
5
7.3
2
7.3
5
7.3
7
3.0
9
3.0
2
2.1
1
1.0
0
2.1
0
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 16
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 17
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
0
2.6
4
2.6
4
3.8
6
6.9
4
6.9
6
7.2
6
7.3
4
7.3
4
7.4
3
7.4
5
3.0
2
3.0
1
2.0
2
1.0
0
2.0
2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 18
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
18.3
06
55.4
41
76.6
82
77.0
00
77.3
17
114
.431
128
.426
130
.184
135
.099
149
.732
161
.585
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 19
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 20
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
18.3
85
76.6
83
77.0
01
77.3
18
124
.863
128
.337
132
.267
136
.382
137
.099
148
.542
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 21
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 22
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 23
10 9 8 7 6 5 4 3 2 1 0 ppm
0.0
0
2.7
1
7.1
2
7.1
3
7.1
5
7.2
6
7.4
7
7.4
8
7.4
8
7.5
0
7.5
7
3.0
2
1.0
3
2.0
0
1.0
1
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 24
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
17.8
52
76.6
81
76.9
99
77.3
17
128
.617
129
.206
129
.557
133
.740
140
.529
142
.889
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 25
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
0
2.6
6
2.6
6
5.5
5
5.5
5
5.7
2
6.1
7
7.2
0
7.2
0
7.2
1
7.2
1
7.2
2
7.2
2
7.2
3
7.2
3
7.2
6
7.3
4
7.3
5
7.3
6
7.3
6
7.3
6
7.3
7
7.3
8
7.3
8
7.5
6
7.5
8
7.6
5
7.6
5
7.6
6
7.6
7
7.6
7
7.6
8
7.6
9
7.6
9
7.7
1
7.7
1
7.7
3
7.7
3
7.7
7
7.7
7
7.7
9
7.7
9
7.8
1
1.6
9
2.1
1
1.0
6
1.0
5
1.0
2
0.5
6
0.5
6
1.0
1
1.0
9
0.6
1
0.5
7
1.0
0
0.6
0
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 26
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
15.8
46
76.6
82
76.9
99
77.3
17
77.4
05
119
.718
121
.834
122
.459
123
.039
124
.729
136
.600
137
.084
138
.220
138
.582
146
.216
148
.964
149
.813
154
.490
154
.609
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 27
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
0
3.8
7
6.9
5
6.9
7
7.2
7
7.5
0
7.5
1
7.5
2
7.5
4
7.9
6
7.9
9
3.0
4
2.1
3
3.0
6
1.0
0
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 28
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
55.4
98
76.6
84
77.0
02
77.3
20
114
.885
122
.498
131
.143
134
.978
139
.014
162
.909
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 29
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0.0
00
0.0
84
0.0
86
7.2
61
7.4
31
7.4
48
7.4
67
7.4
84
7.4
87
7.5
01
7.5
33
7.5
37
7.5
54
7.5
69
7.6
03
7.9
81
8.0
15
6.2
95
1.0
00
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 30
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
83
77.0
01
77.3
19
129
.081
129
.324
129
.977
132
.087
137
.029
139
.015
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 31
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.0
00
0.0
76
2.4
08
7.2
45
7.2
60
7.2
65
7.4
32
7.4
52
7.5
47
7.5
81
7.9
64
7.9
98
3.0
55
2.1
45
2.1
21
1.0
44
1.0
00
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 32
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
21.6
40
76.6
81
76.9
98
77.3
16
127
.251
129
.167
130
.120
136
.263
139
.149
143
.084
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 33
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.0
20
7.2
67
7.5
02
7.5
21
7.5
40
7.5
78
7.5
96
7.6
13
7.6
16
7.6
28
7.6
49
7.6
51
7.6
62
7.7
36
7.7
53
7.9
15
7.9
35
7.9
97
8.0
18
8.1
15
8.1
36
8.8
07
8.8
40
1.1
19
3.2
10
1.0
51
1.1
25
1.0
78
1.0
65
1.0
00
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 34
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
83
77.0
01
77.3
18
122
.918
125
.356
126
.340
126
.753
126
.917
127
.696
129
.018
131
.516
132
.517
133
.716
136
.051
138
.432
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 35
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm
-0.0
00
3.9
32
3.9
47
6.9
12
6.9
32
7.0
16
7.0
19
7.1
69
7.1
89
7.2
78
7.5
23
7.5
57
7.9
49
7.9
83
3.1
28
2.9
99
1.0
90
1.1
45
1.0
56
1.0
39
1.0
00
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 36
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
55.9
56
56.0
37
76.6
81
76.9
99
77.3
17
110
.175
111
.279
122
.743
124
.596
135
.110
139
.286
149
.494
152
.751
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 37
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 38
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 39
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm
0.0
22
0.1
00
7.0
46
7.0
65
7.0
67
7.1
41
7.1
57
7.1
58
7.1
81
7.2
00
7.2
18
7.2
74
7.2
77
7.2
92
7.3
86
7.4
04
7.4
25
7.4
44
7.5
14
7.5
48
7.9
38
7.9
73
2.1
50
2.1
11
1.2
13
1.1
92
3.1
19
1.1
15
1.0
00
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 40
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
81
76.9
99
77.3
17
118
.176
119
.415
121
.996
123
.776
124
.205
130
.036
130
.699
131
.684
137
.575
138
.393
156
.092
158
.346
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 41
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
0
7.2
6
7.6
1
7.6
4
7.6
7
7.6
9
7.7
2
7.7
4
8.0
1
8.0
4
1.0
8
2.1
4
2.0
6
1.0
0
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 42
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
82
77.0
00
77.3
17
119
.401
122
.109
124
.819
126
.293
126
.331
126
.368
126
.404
127
.528
129
.231
132
.964
133
.293
133
.489
133
.621
133
.948
137
.060
138
.874
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 43
9 8 7 6 5 4 3 2 1 0 ppm
0.0
0
7.2
7
7.6
0
7.6
3
7.6
6
7.6
8
7.7
5
7.7
7
7.9
8
8.0
1
1.1
0
2.0
0
2.0
1
1.0
1
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 44
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
83
77.0
01
77.3
18
115
.202
117
.761
129
.363
133
.006
134
.321
136
.525
139
.438
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 45
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
0
7.2
6
7.3
2
7.3
2
7.3
4
7.3
4
7.3
5
7.3
6
7.3
6
7.3
7
7.3
8
7.3
9
7.4
0
7.4
1
7.5
2
7.5
5
7.5
6
7.5
7
7.5
8
7.5
8
7.6
7
7.6
8
7.6
9
7.7
0
8.3
7
8.4
1
2.2
6
1.0
1
1.1
5
1.0
6
1.0
0
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 46
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
83
77.0
01
77.3
18
126
.302
128
.049
128
.438
130
.303
132
.901
133
.972
137
.554
138
.796
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 47
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.0
00
7.1
65
7.1
87
7.1
90
7.2
13
7.2
31
7.2
50
7.2
69
7.4
66
7.4
70
7.4
84
7.4
89
7.5
04
7.5
23
7.5
41
7.7
15
7.7
50
8.0
37
8.0
71
2.1
77
2.1
58
1.0
33
1.0
00
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 48
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
81
76.9
99
77.3
17
116
.487
116
.701
118
.336
118
.456
124
.991
125
.027
131
.338
131
.361
132
.473
133
.630
133
.720
139
.267
139
.385
160
.555
163
.104
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 49
9 8 7 6 5 4 3 2 1 0 ppm
0.0
0
7.2
7
7.4
3
7.4
3
7.4
4
7.4
5
7.4
9
7.4
9
7.5
1
7.5
5
7.5
8
7.9
5
7.9
8
2.0
9
2.1
0
1.1
8
1.0
0
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 50
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
84
77.0
02
77.3
20
128
.501
129
.746
130
.239
137
.397
137
.664
138
.315
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 51
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.0
00
6.5
75
6.5
80
6.5
84
6.5
88
6.8
94
6.9
02
7.2
67
7.5
11
7.5
45
7.5
96
7.5
97
7.7
64
7.7
97
1.0
60
1.0
00
1.0
63
1.0
26
1.0
22
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 52
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
83
77.0
00
77.3
18
113
.315
119
.950
125
.403
134
.901
146
.626
146
.800
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 53
10 9 8 7 6 5 4 3 2 1 0 ppm
0.0
0
7.1
4
7.1
5
7.1
6
7.2
7
7.4
6
7.4
7
7.5
0
7.5
6
7.5
8
8.1
4
8.1
7
1.0
6
2.0
3
1.0
6
1.0
0
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 54
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
84
77.0
01
77.3
19
128
.848
131
.588
132
.054
133
.732
134
.596
135
.323
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 55
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 56
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 57
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm
-0.0
01
0.0
01
6.8
20
6.8
49
6.8
58
6.8
87
7.1
16
7.1
55
7.2
10
7.2
43
7.3
85
7.3
89
7.3
97
7.4
02
7.4
99
7.5
11
7.5
18
7.7
30
7.7
61
7.7
91
1.0
52
1.0
00
1.0
74
3.1
41
2.1
84
1.0
27
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 58
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
76.6
84
77.0
01
77.3
19
120
.529
127
.682
128
.984
130
.273
135
.089
138
.561
139
.118
145
.983
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 59
2a (Mass Spectrum EI)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 60
2b (Mass Spectrum EI)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 61
3d (Mass Spectrum EI)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 62
3h (Mass Spectrum EI)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 63
3i (Mass Spectrum EI)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 64
3j (Mass Spectrum EI)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 65
3l (Mass Spectrum EI)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 66
3n (Mass Spectrum EI)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
Balaji and Prabhu/ Organic Chemistry/IISc
ESI - 67
3p (Mass Spectrum EI)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013