References and Notes
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Typical Experimental Procedure.
The alkene (0.1 mmol) was dissolved in MeOH (7 mL) and tetraethylammonium bromide
(0.1 mmol), diselenide (0.01 mmol) and H2SO4 (1 µL) were added. The electrodes were inserted into the reaction mixture and constant
current of 3 mA applied. After 6 h, electrolysis was stopped and the MeOH removed
in vacuo. The mixture was dissolved in Et2O, washed with NaHCO3 solution and H2O before drying over MgSO4. The products were purified by preparative TLC or column chromatography.
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Spectroscopic data for 7a: 1H NMR (400 MHz, CDCl3): δ = 3.12 (s, 6 H), 3.65 (s, 3 H), 6.24 (d, J = 15.7 Hz, 1 H), 6.73 (d, J = 15.7 Hz, 1 H), 7.20-7.28 (m, 3 H), 7.38-7.40 (m, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 49.7, 51.7, 100.9, 122.0, 126.9, 128.31, 128.33, 139.0, 147.8, 166.7 ppm. IR
(NaCl): ν = 2950, 2832, 1727, 1659, 1449, 1436, 1304, 1276, 1192, 1167, 1072, 1046,
988, 700 cm-1. HRMS: m/z calcd for C13H16O4: 259.0941; found: 259.0941.
<A NAME="RD33405ST-13">13</A>
Spectroscopic data for 3d: 1H NMR (400 MHz, CDCl3): δ = 1.07 (d, J = 6.1 Hz, 3 H), 1.13 (d, J = 6.1 Hz, 3 H), 3.57 (sept, J = 6.1 Hz, 1 H), 3.64 (s, 3 H), 4.95 (dd, J = 5.4, 1.4 Hz, 1 H), 6.02 (dd, J = 15.6, 1.4 Hz, 1 H), 6.91 (dd, J = 15.6, 5.4 Hz, 1 H), 7.19-7.30 (m, 5 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 21.8, 22.6, 51.6, 69.5, 77.8, 120.1, 127.3, 128.0, 128.7, 140.0, 148.8, 166.9
ppm. IR (NaCl): ν = 2971, 1725, 1659, 1453, 1435, 1298, 1272, 1167, 1120, 978, 699
cm-1. HRMS: m/z calcd for C14H18O3: 252.1594; found: 252.1593.
<A NAME="RD33405ST-14">14</A>
Spectroscopic data for 3e: 1H NMR (400 MHz, CDCl3): δ = 2.06 (s, 3 H), 3.67 (s, 3 H), 5.97 (dd, J = 15.7, 1.5 Hz, 1 H), 6.32 (dd, J = 5.0, 1.5 Hz, 1 H), 6.95 (dd, J = 15.7, 5.0 Hz, 1 H), 7.27-7.31 (m, 5 H). 13C NMR (100 MHz, CDCl3): δ = 21.1, 51.8, 74.2, 121.2, 127.4, 128.83, 128.86, 137.1, 144.9, 166.4, 169.7.
IR (NaCl): ν = 2952, 2918, 2849, 1738, 1727, 1662, 1436, 1372, 1310, 1279, 1228, 1197,
1171, 1069, 1022, 980, 699 cm-1. HRMS: m/z calcd for C13H14O4: 252.1230; found: 252.1229.
Diselenides 8 were synthesized according to literature procedures:
<A NAME="RD33405ST-15A">15a</A> Compounds 8a,c:
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Fragale G.
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<A NAME="RD33405ST-15B">15b</A> Compound 8b:
Uehlin L.
Fragale G.
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<A NAME="RD33405ST-15C">15c</A>
For compound 8d see ref. 5e.
<A NAME="RD33405ST-16">16</A> Prepared by reaction of phenyl acetaldehyde and cyanoacetic acid. Spectroscopic
data:
Tsuji Y.
Yamada N.
Tanaka S.
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16
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Keinan E.
Sahai M.
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Nudelman A.
Herzig J.
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<A NAME="RD33405ST-18">18</A>
Spectroscopic data for 7b: 1H NMR (400 MHz, CDCl3): δ = 3.11 (s, 6 H), 5.85 (d, J = 16.2 Hz, 1 H), 6.43 (d, J = 16.2 Hz, 1 H), 7.25-7.38 (m, 5 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 49.8, 100.2, 101.4, 116.8, 126.9, 128.6, 128.8, 137.8, 154.0 ppm. IR (NaCl):
ν = 2916, 2848, 2228, 1732, 1450, 1261, 1226, 1191, 1159, 1071, 1047, 972, 774, 746,
702 cm-1. HRMS: m/z calcd for C12H13NO2: 221.1285; found: 221.1283.
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