Isolation of a 1: 1 oxazole-benzyne cycloadduct. An improved method for generating benzyne and a new approach to isobenzofuran

SE Whitney, B Rickborn

Index: Whitney, Scott E.; Rickborn, Bruce Journal of Organic Chemistry, 1988 , vol. 53, # 23 p. 5595 - 5596

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Citation Number: 24

Abstract

Summary: A dual syringe pump addition procedure for benzyne generation from l- aminobenzotriazole with Pb-(OAc), is applied to 4-phenyloxazole at 0" C, to give the isolable 1: l benzyne/oxazole Diels-Alder adduct in essentially quantitative yield; mild solution thermolysis of this adduct gives isobenzofuran.