학술논문
Effect of chalcogenyl substituent on the course of allyl rearrangement at chalcogenation of 1,3-dichloropropene.
Document Type
Article
Author
Source
Subject
*ORGANOCHLORINE compounds
*REARRANGEMENTS (Chemistry)
*CHALCOGENIDES
*NUCLEOPHILIC substitution reactions
*CARBANIONS
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Language
ISSN
1070-4280
Abstract
Formation of 1,3-dichalcogenylpropene at the treatment of 1,3-dichloropropene with organic dichalcogenides in a redox system hydrazine hydrate-KOH is governed by the possibility of an allyl rearrangement. In the presence of bases this rearrangement proceeds via carbanion partially stabilized by the chalcogenyl substituent. The effectivity of the stabilization and consequently the probability of the rearrangement varies in the series of substituents PhS > BnS > PhSe. In the stage of the direct nucleophilic substitution of chlorine the anion PhSe possesses the highest activity. [ABSTRACT FROM AUTHOR]