Tetrahedron letters

A [2++ 4] polar cycloaddition of α-chlorosulfides with conjugated dienes: one-pot synthesis of 1-acyl-and 1-cyano-1-methylthio-2-vinylcyclopropanes

H Ishibashi, Y Kitano, H Nakatani, M Okada, M Ikeda…

Index: Ishibashi, H.; Kitano, Y.; Nakatani, H.; Okada, M.; Ikeda, M.; et al. Tetrahedron Letters, 1984 , vol. 25, # 38 p. 4231 - 4232

Full Text: HTML

Citation Number: 10

Abstract

Abstract In the presence of SnCl 4, methoxycarbonyl-, acetyl-, benzoyl-, or cyano-substituted chloromethyl methyl sulfide (1–4) undergoes [2++ 4] polar cycloaddition with conjugated dienes to afford the cycloadducts of type 7, which, on treatment with base, are converted into the 1-acyl-or 1-cyano-1-methylthio-2-vinylcyclopropanes 9–10 via the ylide intermediates of type 8.