Journal of the Chemical Society, Perkin Transactions 1

Photochemical reactions of thiobenzamides bearing an allylic substituenton the nitrogen atom: double-bond migration via tandem 1, 4-and1, 6-hydrogen transfer

H Aoyama

Index: Aoyama, Hiromu Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 12 p. 1851 - 1854

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Abstract

N-(2-Phenylprop-2-enyl) thiobenzamides 1a–d underwent double-bond migration on irradiation to give N-(2-phenylprop-1-enyl) thiobenzamides 2a–d via consecutive 1, 4-and 1, 6-hydrogen transfer. Photoreaction of an N-(prop-2-enyl) thiobenzamide 1e and an N-(3- phenylprop-2-enyl) thiobenzamide 1f did not give migration products, but afforded pyrroles 3e and 3f and dealkylation products 4a in low yields.