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

被引：6

作者：

Mori, T

Takamoto, M

Saito, H

Furo, T

Wada, T

Inoue, Y

机构：

[1] Osaka Univ, Dept Mol Chem, Suita, Osaka 5650871, Japan

[2] JST, ICORP, Entropy Control Project, Toyonaka, Osaka 5600085, Japan

来源：

CHEMISTRY LETTERS | 2004年 / 33卷 / 03期

关键词：

D O I：

10.1246/cl.2004.256

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Successful isolation of "ortho" and "para"-acylcyclohexa-dienones 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.

引用

页码：256 / 257

页数：2

共 21 条

[1]

[Anonymous], J PHOTOCHEM PHOTOB C

[2] Investigation of the photo-fries rearrangements of two 2-naphthyl alkanoates by experiment and theory. Comparison with the acid-catalyzed reactions [J].