Efficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide as the Acetylene Source
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1 Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Efficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide as the Acetylene Source Konstantin S. Rodygin, and Valentine P. Ananikov * S1
2 Contents 1. Materials and methods Optimization of reaction conditions Synthetic procedure of scaling experiment Mechanistic studies Preparation of calcium carbide Spectral data and characterization Literature S2
3 1. Materials and methods Calcium carbide was purchased from Acros (97+% purity) and preparation for the reaction was performed as shown on Figure S4. Solvents were dried and purified according to standard procedures. GCMS was performed using a Shimadzu GC- 2010Ultra coupled to a GCMS-QP2010 with an RTX-5ms column employing helium gas as the mobile phase. 1 H, 13 C and 19 F NMR spectra were recorded using a Bruker Avance 400 NMR spectrometer. The data were processed using MestReNova (version 6.0.2) desktop NMR data processing software. Microanalyses (C, H, N) were carried out on a Euro EA3028-HT analyzer. The FE-SEM observations were performed using a Hitachi SU8000 field-emission scanning electron microscope. 2. Optimization of reaction conditions Table S1. Optimization of reaction conditions in the synthesis of vinyl thioesters. [a] Entry Solvent Base Yield (%) [b] 1 DMF Na 2 CO DMF K 2 CO DMF NaOH 89 4 DMF Pyridine 57 5 DMF No base Trace 6 EtOH KOH 5 7 t BuOH KOH 84 8 DCE KOH Trace 9 Dioxane KOH THF KOH Trace 11 No solvent KOH Trace [a] Experimental conditions: powdered CaC 2 (2 mmol); benzenethiol (1 mmol); dried solvent; H 2 O (3 mmol); 100 C, 3 h; [b] Isolated yields. S3
4 3. Synthetic procedure of scaling experiment KOH (60 mmol, 3.36 g), benzenethiol (40 mmol, 4.08 ml), and water (120 mmol, 2.16 ml) were added to a sealed reaction flask (250 ml) with 150 ml DMF under inert atmosphere. After stirring at room temperature for 30 min, powdered calcium carbide (80 mmol, 5.12 g) was added, and the mixture was heated to 100 C with vigorous stirring for 3 h. Then, the mixture was filtered, diluted with aqueous alkaline solution (50 ml), and transferred to a separatory funnel. The layers were separated, and the aqueous layer was extracted with ether (3 50 ml). The organic fractions were combined, washed with water (100 ml), and dried with sodium sulfate. The mixture was filtered, and the solvent was evaporated under reduced pressure. The evaporation temperature was maintained as low as possible to avoid product loss due to volatility of phenyl vinyl sulfide. Distillation of the residue afforded 4.9 g (91-92%) of phenyl vinyl sulfide, bp C/11-12 mm. Caution! A care should be taken with dosing of water and calcium carbide to avoid excessive pressure in the reaction vessel. Acetylene should be slowly released and reacted. S4
5 4. Mechanistic studies (a) Thiovinylation with gaseous acetylene dissolved in DMSO-d6. A modest flow of gaseous acetylene was bubbled through 1 ml of DMSO-d6 for 20 min at room temperature. Then, 1 H and 13 C NMR spectra were recorded for the dissolved acetylene (Figure S1 and S2). Spectral data: 1 H NMR (DMSO-d6, 400 MHz) 2.81 (s). 13 C NMR (DMSO-d6, 100 MHz) Next, KOH (1.5 mmol), benzenethiol (1 mmol), and water (3 mmol) were added to the acetylene solution under inert atmosphere. The mixture was heated to 100 C with vigorous stirring for 3 h. Then, the mixture was analyzed by NMR and GCMS, and formation of phenyl vinyl sulfide 1 was detected. Figure S1. 1 H NMR spectrum of acetylene with 3 J HH = 9 Hz measured in 13 C satellites. S5
6 Figure S2. 13 C NMR spectrum of acetylene. (b) Use of molecular sieves and 1,2-bis(phenylthio)-ethene formation. KOH (1.5 mmol), benzenethiol (1 mmol) and molecular sieves were added to a reaction tube (10 ml) with 1 ml dry DMF under inert atmosphere. After stirring at room temperature for 30 min, powdered calcium carbide (2 mmol) was added, and the mixture was heated to 100 C with vigorous stirring for 3 h. Then, the mixture was diluted with aqueous alkaline solution (10 ml), and the aqueous layer was extracted with diethyl ether (2 10 ml), dried over Na 2 SO 4, and concentrated under vacuum to give a crude product that was analyzed by NMR and GCMS. S6
7 Figure S3. 1,2-bis(phenylthio)ethene. 1 H NMR spectrum of the reaction mixture containing Blue signals indicate the trace amount of phenyl vinyl sulfide formed due to a remaining trace amount of water in the reaction mixture. Red signals correspond to the CH=CH protons; 3 J HH = 8.2 Hz measured in 13 C satellites indicates cis-geometry of the double bond. The obtained spectra agree with the literature data. [1] S7
8 5. Preparation of calcium carbide Calcium carbide as received. Calcium carbide after grinding. Field-Emission Scanning Electron Microscopy (FE-SEM) image of calcium carbide after grinding. Figure S4. Preparation of CaC 2 for the reaction. S8
9 6. Spectral data and characterization phenyl vinyl sulfide (1). 1 H NMR (CDCl 3, 400 MHz) 7.43 (2H, d, J = 7 Hz), 7.36 (2H, t, J = 7 Hz), 7.29 (1H, tt, J = 7 Hz, 1 Hz), 6.58 (1H, dd, J = 17, 10 Hz), 5.39 (1H, d, J = 10 Hz), 5.38 (1H, d, J = 17 Hz). 13 C NMR (CDCl 3, 100 MHz) 134.3, 131.9, 130.6, 129.2, 127.1, MS: m/z (% of max intensity) 51 (28), 58 (10), 65 (25), 66 (16), 67 (12), 69 (10), 77 (21), 91 (100), 109 (11), 135 (75), 136 (62). Anal. calcd (%) for C 8 H 8 S: C, 70.54; H, Found (%): C, 70.48; H, Figure S5. 1 H NMR spectrum of phenyl vinyl sulfide (1). Figure S6. 13 C NMR spectrum of phenyl vinyl sulfide (1). 2-methylphenyl vinyl sulfide (2). 1 H NMR (CDCl 3, 400 MHz) (1H, m), (3H, m), 6.50 (1H, dd, J = 17, 10 Hz), 5.34 (1H, d, J = 10 Hz), 5.19 (1H, d, J = 17 Hz), 2.43 (3H, s). 13 C NMR (CDCl 3, 100 MHz) 139.5, 132.6, 131.9, 131.5, 130.4, 127.7, 126.7, 114.4, MS: m/z (% of S9
10 max intensity) 45 (20), 65 (17), 77 (18), 91 (53), 134 (17), 135 (100), 149 (15), 150 (59). Anal. calcd (%) for C 9 H 10 S: C, 71.95; H, Found (%): C, 71.99; H, Figure S7. 1 H NMR spectrum of 2-methylphenyl vinyl sulfide (2). Figure S8. 13 C NMR spectrum of 2-methylphenyl vinyl sulfide (2). 3-methylphenyl vinyl sulfide (3). 1 H NMR (CDCl 3, 400 MHz) (3H, m), (1H, d, J = 7 Hz), 6.58 (1H, dd, J = 17, 10 Hz), 5.38 (1H, d, J = 17 Hz), 5.37 (1H, d, J = 10 Hz), 2.37 (3H, s). 13 C NMR (CDCl 3, 100 MHz) 139.0, 134.0, 132.1, 131.1, 129.0, 128.0, 127.5, 115.3, MS: m/z (% of max intensity) 65 (20), 74 (18), 77 (21), 79 (16), 91 (56), 105 (41), 134 (28), 135 (100), 149 (23), 150 (71). Anal. calcd (%) for C 9 H 10 S: C, 71.95; H, Found (%): C, 71.90; H, Figure S9. 1 H NMR spectrum of 3-methylphenyl vinyl sulfide (3). S10
11 Figure S C NMR spectrum of 3-methylphenyl vinyl sulfide (3). 4-methylphenyl vinyl sulfide (4). 1 H NMR (CDCl 3, 400 MHz) 7.33 (2H, d, J = 8 Hz), 7.18 (2H, d, J = 8 Hz), 6.54 (1H, dd, J = 17, 10 Hz), 5.32 (1H, d, J = 10 Hz), 5.28 (1H, d, J = 17 Hz), 2.38 (3H, s). 13 C NMR (CDCl 3, 100 MHz) 137.4, 132.7, 131.3, 130.2, 129.9, 114.2, MS: m/z (% of max intensity) 45 (7), 51 (7), 63 (7), 65 (34), 89 (8), 90 (6), 91 (100), 92 (25), 104 (8), 150 (32). Anal. calcd (%) for C 9 H 10 S: C, 71.95; H, Found (%): C, 71.88; H, Figure S11. 1 H NMR spectrum of 4-methylphenyl vinyl sulfide (4). S11
12 Figure S C NMR spectrum of 4-methylphenyl vinyl sulfide (4). 2-chlorophenyl vinyl sulfide (5). 1 H NMR (CDCl 3, 400 MHz) 7.42 (1H, dd, J = 8 Hz, 1.5 Hz), 7.39 (1H, dd, J = 8 Hz, 1.5 Hz),, 7.27 (1H, td, J = 8 Hz, 1.5 Hz), 7.20 (1H, td, J = 8 Hz, 1.5 Hz), 6.54 (1H, dd, J = 17, 9 Hz), 5.55 (1H, d, J = 9 Hz), 5.53 (1H, d, J = 17 Hz). 13 C NMR (CDCl 3, 100 MHz) 134.3, 133.9, 130.3, 129.8, 129.5, 127.7, 127.3, MS: m/z (% of max intensity) 67(15), 69 (12), 75 (13), 91 (48), 108 (24), 109 (14), 125 (15), 134 (26), 135 (100), 136 (11), 170 (36), 172 (14). Anal. calcd (%) for C 8 H 7 ClS: C, 56.30; H, Found (%): C, 56.25; H, Figure S13. 1 H NMR spectrum of 2-chlorophenyl vinyl sulfide (5). S12
13 Figure S C NMR spectrum of 2-chlorophenyl vinyl sulfide (5). 3-chlorophenyl vinyl sulfide (6). 1 H NMR (CDCl 3, 400 MHz) 7.38 (1H, t, J = 2 Hz), (3H, m), 6.54 (1H, dd, J = 17, 10 Hz), 5.48 (1H, d, J = 17 Hz), 5.48 (1H, d, J = 10 Hz). 13 C NMR (CDCl 3, 100 MHz) 136.8, 134.9, 130.5, 130.1, 129.4, 127.8, 127.0, MS: m/z (% of max intensity) 67 (16), 75 (19), 91 (47), 108 (19), 109 (12), 125 (21), 134 (30), 135 (100), 136 (11), 170 (37), 172 (13). Anal. calcd (%) for C 8 H 7 ClS: C, 56.30; H, Found (%): C, 56.21; H, Figure S15. 1 H NMR spectrum of 3-chlorophenyl vinyl sulfide (6). S13
14 Figure S C NMR spectrum of 3-chlorophenyl vinyl sulfide (6). 4-chlorophenyl vinyl sulfide (7). 1 H NMR (CDCl 3, 400 MHz) 7.33 (4H, br. s), 6.51 (1H, dd, J = 17, 10 Hz), 5.41 (1H, d, J = 10 Hz), 5.38 (1H, d, J = 17 Hz). 13 C NMR (CDCl 3, 100 MHz) 133.3, 132.8, 131.8, 131.3, 129.3, MS: m/z (% of max intensity) 50 (11), 63 (10), 67 (15), 75 (20), 91 (46), 108 (26), 109 (15), 125 (26), 134 (28), 135 (100), 136 (11), 170 (45), 172 (16). Anal. calcd (%) for C 8 H 7 ClS: C, 56.30; H, Found (%): C, 56.38; H, Figure S17. 1 H NMR spectrum of 4-chlorophenyl vinyl sulfide (7). S14
15 Figure S C NMR spectrum of 4-chlorophenyl vinyl sulfide (7). Hexyl vinyl sulfide (8). 1 H NMR (CDCl 3, 400 MHz) 6.38 (1H, dd, J = 17, 10 Hz), 5.20 (1H, d, J = 10 Hz), 5.12 (1H, d, J = 17 Hz), 2.72 (2H, t, J = 7), 1.66 (2H, quint, J = 7), 1.43 (2H, quint, J = 7 Hz), (4H, m), 0.91 (3H, t, J = 7 Hz). 13 C NMR (CDCl 3, 100 MHz) 132.6, 110.3, 31.4, 31.4, 29.0, 28.6, 22.5, MS: m/z (% of max intensity) 41 (45), 43 (82), 45 (31), 55 (37), 56 (34), 60 (100), 61 (25), 73 (30), 115 (25), 144 (27). Anal. calcd (%) for C 8 H 16 S: C, 66.60; H, Found (%): C, 66.58; H, Figure S19. 1 H NMR spectrum of hexyl vinyl sulfide (8). S15
16 Figure S C NMR spectrum of hexyl vinyl sulfide (8). 4-fluorophenyl vinyl sulfide (9). 1 H NMR (CDCl 3, 400 MHz) 7.41 (2H, m), 7.07 (2H, m), 6.50 (1H, dd, J = 17, 10 Hz), 5.34 (1H, d, J = 10 Hz), 5.25 (1H, d, J = 17 Hz). 13 C NMR (CDCl 3, 100 MHz) (d, J = 247 Hz), (d, J = 8 Hz), 132.4, (d, J = 3 Hz), (d, J = 22 Hz), F NMR (CDCl 3, 376 MHz) (s). MS: m/z (% of max intensity) 57 (11), 69 (11), 75 (16), 83 (34), 84 (13), 108 (14), 109 (100), 153 (80), 154 (75), 155 (10). Anal. calcd (%) for C 8 H 7 FS: C, 63.31; H, Found (%): C, 63.28; H, Figure S21. 1 H NMR spectrum of 4-fluorophenyl vinyl sulfide (9). S16
17 Figure S C NMR spectrum of 4-fluorophenyl vinyl sulfide (9). Figure S F NMR spectrum of 4-fluorophenyl vinyl sulfide (9). 2-aminophenyl vinyl sulfide (10). 1 H NMR (CDCl 3, 400 MHz) 7.40 (1H, dd, J = 8 Hz, 1.5Hz), 7.22 (1H, td, J = 8 Hz, 1.5Hz), 6.79 (1H, d, J = 7 Hz), 6.76 (1H, t, J = 7 Hz), 6.35 (1H, dd, J = 16, 10 Hz), 5.23 (1H, d, J = 10 Hz), 4.99 (1H, d, J = 16 Hz), 4.28 (2H, br. s). 13 C NMR (CDCl 3, 100 MHz) 148.2, 136.4, 131.1, 130.8, 118.8, 115.3, 113.8, MS: m/z (% of max intensity) 65 (21), 80 (52), 91 (17), 106 (15), 109 (17), 117 (20), 118 (17), 136 (100), 150 (18), 151 (68). Anal. calcd (%) for C 8 H 9 NS: C, 63.54; H, 6.00; N, Found (%): C, 63.58; H, 6.06; N, S17
18 Figure S24. 1 H NMR spectrum of 2-aminorophenyl vinyl sulfide (10). Figure S C NMR spectrum of 2-aminorophenyl vinyl sulfide (10). 3-aminophenyl vinyl sulfide (11). 1 H NMR (CDCl 3, 400 MHz) 7.13 (1H, t, J = 8 Hz), 6.80 (1H, ddd, J = 8 Hz, 1.5 Hz, 1 Hz), 6.73 (1H, t, J = 2 Hz), 6.59 (1H, dm, J = 8 Hz, <3 Hz), 6.57 (1H, dd, J = 17, 9 Hz), 5.39 (1H, d, J = 17), 5.37 (1H, d, J = 9), 3.71 (2H, br. s). 13 C NMR (CDCl 3, 100 MHz) 147.1, 135.2, 131.9, 129.9, 120.3, 116.5, 115.5, MS: m/z (% of max intensity) 65 (10), 80 (36), 106 (49), 118 (10), 119 (13), 124 (29), 150 (58), 151 (100), 152 (12). Anal. calcd (%) for C 8 H 9 NS: C, 63.54; H, 6.00; N, Found (%): C, 63.49; H, 5.94; N, S18
19 Figure S26. 1 H NMR spectrum of 3-aminorophenyl vinyl sulfide (11). Figure S C NMR spectrum of 3-aminorophenyl vinyl sulfide (11). 4-aminophenyl vinyl sulfide (12). 1 H NMR (CDCl 3, 400 MHz) 7.27 (2H, d, J = 8 Hz), 6.69 (2H, d, J = 8 Hz), 6.48 (1H, dd, J = 16, 10 Hz), 5.19 (1H, d, J = 10 Hz), 5.06 (1H, d, J = 16 Hz), 3.80 (2H, br. s). 13 C NMR (CDCl 3, 100 MHz) 146.7, 134.7, 134.5, 120.0, 115.7, MS: m/z (% of max intensity) 65 (24), 80 (25), 91 (13), 106 (60), 117 (17), 118 (12), 149 (14), 150 (100), 151 (97), 152 (13). Anal. calcd (%) for C 8 H 9 NS: C, 63.54; H, 6.00; N, Found (%): C, 63.46; H, 5.95; N, Figure S28. 1 H NMR spectrum of 4-aminorophenyl vinyl sulfide (12). S19
20 Figure S C NMR spectrum of 4-aminorophenyl vinyl sulfide (12). Cyclohexyl vinyl sulfide (13). 1 H NMR (CDCl 3, 400 MHz) 6.40 (1H, dd, J = 17, 10 Hz), 5.24 (1H, d, J = 17 Hz), 5.22 (1H, d, J = 10 Hz), (1H, m), (2H, m), (2H, m), (1H, m), (5H, m). 13 C NMR (CDCl 3, 100 MHz) 131.6, 112.4, 44.37, 33.4, 26.0, MS: m/z (% of max intensity) 41 (51), 54 (20), 55 (100), 60 (31), 61 (16), 67 (72), 80 (20), 81 (30), 82 (83), 83 (80), 142 (36). Anal. calcd (%) for C 8 H 14 S: C, 67.54; H, Found (%): C, 67.51; H, Figure S30. 1 H NMR spectrum of cyclohexyl vinyl sulfide (13). S20
21 Figure S C NMR spectrum of cyclohexyl vinyl sulfide (13). Dodecyl vinyl sulfide (14). 1 H NMR (CDCl 3, 400 MHz) 6.39 (1H, dd, J = 17, 10 Hz), 5.20 (1H, d, J = 10 Hz), 5.12 (1H, d, J = 17 Hz), 2.72 (2H, t, J = 8), 1.67 (2H, quint, J = 8), 1.42 (2H, quint, J = 8 Hz), (16H, m), 0.91 (3H, t, J = 7 Hz). 13 C NMR (CDCl 3, 100 MHz) 132.6, 110.3, 31.9, 31.4, 29.6, 29.6, 29.6, 29.5, 29.3, 29.2, 29.1, 28.9, 22.7, MS: m/z (% of max intensity) 41 (74), 43 (82), 55 (92), 57 (61), 60 (100), 61 (35), 67 (32), 68 (36), 69 (59), 81 (32), 82 (37), 83 (35), 87 (68), 101 (48), 115 (33), 199 (45), 228 (12). Anal. calcd (%) for C 14 H 28 S: C, 73.61; H, Found (%): C, 73.57; H, Figure S32. 1 H NMR spectrum of dodecyl vinyl sulfide (14). S21
22 Figure S C NMR spectrum of dodecyl vinyl sulfide (14). Benzyl vinyl sulfide (15). 1 H NMR (CDCl 3, 400 MHz) (4H, m), (1H, m), 6.40 (1H, dd, J = 17, 10 Hz), 5.24 (1H, d, J = 10 Hz), 5.21 (1H, d, J = 10 Hz), 3.96 (2H, s). 13 C NMR (CDCl 3, 100 MHz) 137.2, 132.0, 128.8, 128.6, 127.3, 111.7, MS: m/z (% of max intensity) 45 (7), 51 (7), 63 (7), 65 (34), 89 (8), 90 (6), 91 (100), 92 (25), 104 (8), 150 (32). Anal. calcd (%) for C 9 H 10 S: C, 71.95; H, Found (%): C, 71.90; H, Figure S34. 1 H NMR spectrum of benzyl vinyl sulfide (15). S22
23 Figure S C NMR spectrum of benzyl vinyl sulfide (15). 3-methylbutyl vinyl sulfide (16). 1 H NMR (CDCl 3, 400 MHz) 6.39 (1H, dd, J = 17, 10 Hz), 5.21 (1H, d, J = 10 Hz), 5.12 (1H, d, J = 17 Hz), 2.72 (2H, m, J = 7 Hz), 1.71 (1H, o, J = 7 Hz), (2H, m), 0.95 (6H, d, J = 7 Hz). 13 C NMR (CDCl 3, 100 MHz) 132.5, 110.3, 37.9, 29.3, 27.5, MS: m/z (% of max intensity) 41 (44), 42 (28), 43 (76), 45 (42), 55 (100), 59 (27), 60 (92), 70 (92), 73 (30), 74 (42), 115 (26), 130 (42). Anal. calcd (%) for C 7 H 14 S: C, 64.55; H, Found (%): C, 64.50; H, Figure S36. 1 H NMR spectrum of 3-methylbutyl vinyl sulfide (16). S23
24 Figure S C NMR spectrum of 3-methylbutyl vinyl sulfide (16). 2-pyridyl vinyl sulfide (17). 1 H NMR (CDCl 3, 400 MHz) 8.48 (1H, ddd, J = 5 Hz, 1.5 Hz, 1 Hz), 7.54 (1H, td, J = 8 Hz, 2 Hz), 7.21 (1H, dt, J = 8 Hz, 1 Hz), 7.14 (1H, dd, J = 17, 10 Hz), 7.05 (1H, ddd, J = 8 Hz, 5 Hz, 1 Hz), 5.61 (1H, d, J = 17 Hz), 5.54 (1H, d, J = 10 Hz). 13 C NMR (CDCl 3, 100 MHz) 157.7, 149.8, 136.4, 128.1, 122.1, 120.2, MS: m/z (% of max intensity) 51 (23), 52 (19), 58 (8), 67 (18), 78 (25), 79 (29), 111 (10), 136 (100), , 138 (7). Anal. calcd (%) for C 7 H 7 NS: C, 61.28; H, 5.14; N, Found (%): C, 61.22; H, 5.18; N, Figure S38. 1 H NMR spectrum of 2-pyridyl vinyl sulfide (17). S24
25 Figure S C NMR spectrum of 2-pyridyl vinyl sulfide (17). 3-fluorophenyl vinyl sulfide (18). 1 H NMR (CDCl 3, 400 MHz) 7.31 (1H, td, J = 7 Hz, 6 Hz), 7.16 (1H, ddd, J = 8 Hz, 1 Hz, <1Hz), 7.11 (1H, dt, J = 9 Hz, 2 Hz), 6.96 (1H, tdd, J = 8 Hz, 2.5 Hz, 1 Hz), 6.56 (1H, dd, J = 17, 9 Hz), 5.49 (1H, d, J = 17 Hz), 5.48 (1H, d, J = 9 Hz). 13 C NMR (CDCl 3, 100 MHz) (d, J = 248 Hz), (d, J = 8 Hz), 130.5, (d, J = 8 Hz), (d, J = 3 Hz), 117.6, (d, J = 23 Hz), (d, J = 21 Hz). 19 F NMR (CDCl 3, 376 MHz) (s). MS: m/z (% of max intensity) 75 (17), 83 (49), 84 (16), 108 (18), 109 (100), 153 (89), 154 (97). Anal. calcd (%) for C 8 H 7 FS: C, 63.31; H, Found (%): C, 63.24; H, Figure S40. 1 H NMR spectrum of 3-fluorophenyl vinyl sulfide (18). S25
26 Figure S C NMR spectrum of 3-fluorophenyl vinyl sulfide (18). Figure S F NMR spectrum of 3-fluorophenyl vinyl sulfide (18). Phenyl vinyl selenide (19). 1 H NMR (CDCl 3, 400 MHz) (2H, m), (3H, m), 6.87 (1H, dd, J = 17, 9 Hz), 5.81 (1H, d, J = 9 Hz; 2 J SeH = 16 Hz), 5.57 (1H, d, J = 17 Hz; 2 J SeH = 5 Hz). 13 C NMR (CDCl 3, 100 MHz) 133.1, 129.3, 127.7, 127.5, MS: m/z (% of max intensity) 50 (21), 51 (48), 77 (100), 78 (99), 91 (37), 102 (15), 103 (57), 104 (87), 180 (22), 181 (36), 182 (36), 183 (57), 184 (66). Anal. calcd (%) for C 8 H 8 Se: C, 52.47; H, Found (%): C, 52.41; H, Figure S44. 1 H NMR spectrum of phenyl vinyl selenide (19). S26
27 Figure S C NMR spectrum of phenyl vinyl selenide (19). 7. Literature [1] (a) C. Gómez, B. Maciá, M. Yus, Tetrahedron 2005, 16, (b) A. L. J. Beckwith, P. E. Pigou, Aust. J. Chem. 1986, 39, S27
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