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Paper | Regular issue | Vol 24, No. 4, 1986, pp.1013-1018
Published online, 1st January, 1970
DOI: 10.3987/R-1986-04-1013
Reactivity of Heterocyclic Ambident S···N Anions in SRN1 Substitution Reactions

Monique Meyer, André Samat, and Michel Chanon*

*U.A. 126 C.N.R.S., Laboratoire de Chimie Inorganique, Université d‘Aix-Marseille III, rue H. Poincaré, 13397 Marseille Cedex 13, France

Abstract

Ambident anions of 2-mercaptoazoles react, under photo-stimulation conditions, with α,p-dinitrocumene according to an SRN1 mechanism (short chain) leading to S-alkylated compounds in agreement with a kinetically controlled reaction. Regioselectivity is governed by nucleophilicity and not by the basicity of the heteroatom. The N-alkylation observed in the case of 2-mercaptoimidazole proceeds from a new photochemical rearrangement with homolytic cleavage of the C-S bond followed by the recombination of the α,p-dinitrocumyl radical with the ambident heterocyclic radicals.