Tetrahedron

Nucleophilic Reactions in ethylenic derivatives—X: Reactions of nitrobromostyrenes with methoxide and thiophenoxide ions

G Marchese, G Modena, F Naso

Index: Marchese,G. et al. Tetrahedron, 1968 , vol. 24, p. 663 - 674

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Citation Number: 16

Abstract

The reactions of cis and trans p-nitro-β-bromostyrene and 2-4-dinitro-β-bromostyrene with methoxide and thiophenoxide ions in methanol have been studied and their rates measured. Whereas the thiophenoxide ion reacts by direct substitution with both cis and trans isomers, yielding the corresponding phenylmercaptoethylenes with retention of configuration, the methoxide ion yields with cis isomers p-nitro and 2-4- ...