Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane

Masahito Ochiai, Akira Yoshimura, Md Mahbubul Hoque, Takuji Okubo, Motomichi Saito, Kazunori Miyamoto

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Oxidation of primary aliphatic aldehydes with p- trifluoromethylphenyl(difluoro)-λ 3-bromane in dichloromethane at 0 °C afforded acid fluorides selectively in good yields, while that of aromatic aldehydes in chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.

Original languageEnglish
Pages (from-to)5568-5571
Number of pages4
JournalOrganic Letters
Volume13
Issue number20
DOIs
Publication statusPublished - 21 Oct 2011
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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