Remarkable differences in photo and thermal (acid-catalyzed) reactivities between ortho-and para-acylcyclohexadienones as essential factors determining the overall efficiency of the photo-fries rearrangement

Tadashi Mori, Makoto Takamoto, Hideaki Saito, Takahiro Furo, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Successful isolation of "ortho" and "para"- acylcyclohexadienones allowed us to comparatively study their ground- and excited-state behavior under a variety of conditions. In neutral solutions, the two isomeric cyclohexdienones showed completely different reactivities for photochemical and thermal reactions, while in acidic methanol both quantitatively afforded the corresponding transesterification product and naphthol. These studies help us understand the detailed photo-Fries rearrangement mechanism, which involves several crucial photochemical and thermal steps.

Original languageEnglish
Pages (from-to)256-257
Number of pages2
JournalChemistry Letters
Volume33
Issue number3
DOIs
Publication statusPublished - 2004 Mar 1
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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