Perfect switching of photoreactivity by acid: Photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate

Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

(matrix presented) Mesityl cyclohexanecarboxylate has been photodecarboxylated upon excitation at 254 nm to form cyclohexylmesitylene in good yield in neutral acetonitrile solutions. In the presence of a catalytic amount of the acid and ethanol as a nucleophile, however, the same compound undergoes facile transesterification upon irradiation, affording its ethyl ester in almost quantitative yield.

Original languageEnglish
Pages (from-to)3401-3404
Number of pages4
JournalOrganic letters
Volume2
Issue number21
DOIs
Publication statusPublished - 2000 Oct 19

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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