Novel parallel reaction between a [1,5] sigmatropic alkylthio shift and a [1,5] sigmatropic hydrogen shift observed in a 2H-azepine ring

Yasuhiro Kubota, Kyosuke Satake, Hideki Okamoto, Masaru Kimura

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

Although heating 2-methoxy-2H-azepine results in a [1,5] sigmatropic hydrogen shift, heating 2-propylthio-2H-azepine results in not only a [1,5] sigmatropic hydrogen shift but also a [1,5] sigmatropic propylthio shift. Kinetic measurements reveal that migratory aptitudes increase in the order of MeO < H, PrS. These [1,5] sigmatropic shifts are discussed on the basis of ab initio DFT calculations.

Original languageEnglish
Pages (from-to)5469-5472
Number of pages4
JournalOrganic Letters
Volume8
Issue number24
DOIs
Publication statusPublished - Nov 23 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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