… Cycloadducts. III. Reinvestigation of the Base-Induced Isomerization of the 1: 1-C= C-Adducts of Aromatic Nitrile Oxides with 2, 5-and 2, 6-Dialkyl-Substituted p- …

T Mukawa, Y Inoue, S Shiraishi

Index: Mukawa, Takashi; Inoue, Yukihiko; Shiraishi, Shinsaku Bulletin of the Chemical Society of Japan, 1999 , vol. 72, # 11 p. 2549 - 2556

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Citation Number: 6

Abstract

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, ie, Et, i-Pr, t-Bu, and Bn at the bridgehead ...