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

doi:10.1246/cl.2004.256

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

IMRAM - Division of Organic- and Biomaterials Research

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	256-257
Number of pages	2
Journal	Chemistry Letters
Volume	33
Issue number	3
DOIs	https://doi.org/10.1246/cl.2004.256
Publication status	Published - 2004 Mar

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title = "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",

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.",

author = "Tadashi Mori and Makoto Takamoto and Hideaki Saito and Takahiro Furo and Takehiko Wada and Yoshihisa Inoue",

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pages = "256--257",

journal = "Chemistry Letters",

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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. / Mori, Tadashi; Takamoto, Makoto; Saito, Hideaki et al.
In: Chemistry Letters, Vol. 33, No. 3, 03.2004, p. 256-257.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 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

AU - Mori, Tadashi

AU - Takamoto, Makoto

AU - Saito, Hideaki

AU - Furo, Takahiro

AU - Wada, Takehiko

AU - Inoue, Yoshihisa

PY - 2004/3

Y1 - 2004/3

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AB - 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.

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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

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