Reactions of 1,2-dinitro- and 1-nitro-2-sulfonylethenes with some binucleophiles

Abstract

SHORT COMMUNICATIONSThe presence in dinitroethene and nitrosulfonylethene molecules of a strong electron-withdrawing and nucleofugal substituent in the β-position with respect to the conjugated nitro group determines high reactivity of these compounds toward nucleophilic reagents and is responsible for predominant formation of replacement products in such reactions [1][2][3]. We previously reported on the reactions of dinitro-and nitrosulfonylethenes with such difunctional nucleophiles as hydrazine [4], thiourea, and N,N′-diphenylthiourea [5]. In the present communication we describe reactions of nitroethenes I-IV with phenylhydrazine, o-aminobenzenethiol, and 6-amino-1,3-benzothiazole-2-thiol. The two latter reagents are interesting due to the presence in their molecules of two potential reaction centers of different natures. We have found no published data on relative nucleophilic reactivity of these reagents. VIII, the latter being formed as two stereoisomers (Scheme 1).