Bulletin of the Chemical Society of Japan p. 2549 - 2556 (1999)
Update date:2022-08-04
Topics:
Mukawa, Takashi
Inoue, Yukihiko
Shiraishi, Shinsaku
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.
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