Reversible intramolecular 1,3-chlorine migration in the triad 'carbon-carbon-sulfur'

Vera Ya Popkova, Victor M. Anisimov, Georgii N. Dolenko, Mikhail N. Semenenko, Vladimir M. Fedoseev

Research output: Contribution to journalArticle

Abstract

An intramolecular 1,3-chlorine migration in the triad 'carbon-carbon- sulfur' with nucleophilic solvent or catalyst assistance is proposed as a mechanism for the perfluoro-2-methylpent-2-ene-3-sulfenyl chloride 1 ⇌ 2-chloroperfluoro-2-methylpentane-3-thione 2 tautomerism. The data from radionuclidic investigations were used to elucidate the aforementioned mechanism. The results of MNDO calculations showed that the solvation lowers the height of the reaction barriers of both direct and reverse reactions and brings about different reaction pathways for these two processes, providing greater assistance to the 1 → 2 than to the 2 → 1 reaction.

Original languageEnglish (US)
Pages (from-to)1375-1379
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number7
DOIs
StatePublished - 1995
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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