Isolation of cyclohexadienone intermediates in the photo-fries rearrangement of 2,4-dimethylnaphth-1-yl and 1,4-dimethylnaphth-2-yl 2,4,6-trimethylbenzoates

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

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10 Citations (Scopus)

Abstract

Labile cyclohexadienones were isolated for the first time in good yields in the photo-Fries rearrangement of partially blocked naphthyl esters. Upon direct excitation at 313 nm, 1,4-dimethylnaphth-2-yl and 2,4-dimethylnaphth-1-yl 2,4,6-trimethylbenzoates afforded 1-acyl-2-naphthalenone and 2- and 4-acyl-1-naphthalenones, respectively. This isolation is of particular importance as a direct mechanistic proof and also as a convenient route to these thermally less-accessible compounds.

Original languageEnglish
Pages (from-to)254-255
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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