The Reaction of Nitrile Oxide-Quinone Cycloadducts. III. Reinvestigation of the Base-Induced Isomerization of the 1

The structure of the product obtained by the base-induced isomerization of the 1,3-dipolar cycloadduct of 2,5-di-t-butyl-p-benzoquinone with 2,6-dichlorobenzonitrile oxide was determined by X-ray analysis. The t-butyl group at the bridgehead position of the 1,3-dipolar cycloadduct migrated to the ne...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 1999-11, Vol.72 (11), p.2549
Main Authors: Mukawa, Takashi, Inoue, Yukihiko, Shiraishi, Shinsaku
Format: Article
Language:English
Online Access:Get full text
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Summary:The structure of the product obtained by the base-induced isomerization of the 1,3-dipolar cycloadduct of 2,5-di-t-butyl-p-benzoquinone with 2,6-dichlorobenzonitrile oxide was determined by X-ray analysis. The t-butyl group at the bridgehead position of the 1,3-dipolar cycloadduct migrated to the neighboring carbonyl carbon atom. This base-induced rearrangement took place with a bulky group, i. e., Et, i-Pr, t-Bu, and Bn at the bridgehead position of nitrile oxide-quinone cycloadducts in an alcoholic media. The driving force of this reaction is considered to be due to stabilization by aromatization from isoxazoline derivatives to isoxazole-fused p-quinol derivatives.
ISSN:0009-2673
1348-0634