Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes: A non-singlet-oxygen mechanism

Tadashi Mori, Makoto Takamoto, Yoshimasa Tate, Junya Shinkuma, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

α-Methylstyrene (1) was photooxidized with oxygen in the presence of a series of alkylated dimethoxybenzenes as a sensitizer in acetonitrile, affording the cleaved ketone (2), epoxide (3) as well as a small amount of the ene product (4) in ca. 1:1:0.04 ratio. A non-singlet-oxygen mechanism is proposed, in which an excited sensitizer is quenched by oxygen to produce a sensitizer radical cation and a superoxide ion (O2·-), the former of which oxidizes 1, while O2·- reacts with the resulting 1·+ to give the major oxidation products.

Original languageEnglish
Pages (from-to)2505-2508
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number13
DOIs
Publication statusPublished - 2001 Mar 26
Externally publishedYes

Keywords

  • Dimethoxybenzenes
  • Electron transfer oxidation
  • Molecular oxygen
  • Non-singlet-oxygen mechanism
  • α-methylstyrene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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