Organic letters

Alkenylthioimidoyl Radicals: Competition between β-Scission and Cyclization to Dihydrothiophen-2-ylidene-amines

M Minozzi, D Nanni, JC Walton

Index: Minozzi, Matteo; Nanni, Daniele; Walton, John C. Organic Letters, 2003 , vol. 5, # 6 p. 901 - 904

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Citation Number: 27

Abstract

But-3-enylthioimidoyl radicals were shown by EPR spectroscopy and end product analysis to ring-close predominantly in the 5-exo mode with a rate constant of 2.4× 104 s-1 at 300 K to afford substituted dihydrothiophenylmethyl radicals. This ring closure was in competition with dissociation to but-3-enyl radicals and an isothiocyanate. The dissociation predominated at temperatures above ca. 300 K.