Benzyne-oxazole cycloadducts: isolation and retro-Diels-Alder reactions

SE Whitney, M Winters, B Rickborn

Index: Whitney, Scott E.; Winters, Michael; Rickborn, Bruce Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 929 - 935

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Citation Number: 53

Abstract

A literature procedure for generating benzyne from 1-aminobenzotriazole and lead tetraacetate was modified by the use of two syringe pumps to effect simultaneous addition through opposing ports of a three-neck flask. Applied to the reaction of benzyne with 4- phenyloxazole at 0" C, this modification resulted in essentially quantitative formation of cycloadduct. Retro-Dieh-Alder expulsion of benzonitrile with concurrent formation of ...

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