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Miscellany

[4π + 2π] Cycloadditions of N-Acyl-Thioformamides

Pages 245-258 | Published online: 30 Jul 2008

REFERENCES AND NOTES

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  • 2cis : 1H NMR : 2.1 and 2.2 (2 s, 6H, 2 Me), 4.0 (d, 1H, CHCN, J = 6 Hz), 5.4 (dd, 1H, CHOR, J = 0.5 and J = 6 Hz), 5.9-6.2 (m, 3H, SCHOR, CH=CH). 13C NMR : 20.7, 20.8, 25.5, 65.5, 67.2, 116.0 (CN), 126.0, 130.0, 169.9, 170.1 ppm. 2trans : 1H NMR : 2.1 and 2.2 (2 s, 6H, 2 Me), 4.1 (d, 1H, CHCN, J = 11 Hz), 5.7 (d, 1H, CHOR, J = 11 Hz), 5.9-6.0 (m, 2H, CH=CH), 6.1 (d, 1H, SCHOR). 3cis: 1H NMR : 0.1 and 0.15 (2 s, 12H, Me), 0.9 and 1.0 (2 s, 18H, t-Bu), 3.5 (d, 1H, CHCN, J = 4.7 Hz), 4.3 (m, 1H, CHOR), 5.2 (d, 1H, SCHOR), 5.7 (m, 2H, CH=CH). MS (CI) : m/z = 403 (M + NH4+). 3trans : 1H NMR : 0.1 and 0.14 (2 s, 12H, Me), 0.9 and 1.0 (2 s, 18H, t-Bu), 3.8 (d, 1H, CHCN, J = 10.3 Hz), 4.4 (dd, 1H, CHOR, J = 0.5 and J = 10.3 Hz), 5.1 (d, 1H, SCHOR), 5.7 (m, 2H, CH=CH). MS (CI) : m/z = 403 (M + NH4+.
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  • Measured by 19F-NMR.
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