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Preparation of 1,2-Oxazetidines from Styrenes and Arylamines via a Peroxide-Mediated [2 + 1 + 1] Cycloaddition Reaction

Weibing Liu* , Cui Chen, Peng Zhou and Hua Tan

*College of Chemical Engineering, Guangdong University of Petrochemical Technology, 2 Guandu Road, Maoming 525000, P.R. China, Email: lwb409gdupt.edu.cn

W. Liu, C. Chen, P. Zhou, H. Tan, Org. Lett., 2017, 19, 5830-5832.

DOI: 10.1021/acs.orglett.7b02796 (free Supporting Information)



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Abstract

A [2 + 1 + 1] radical tandem cycloaddition of styrenes, arylamines, and tert-butyl hydroperoxide enables a regioselective synthesis of polysubstituted 1,2-oxazetidines. TBHP was employed in this conversion not only as the oxidant but also as the oxygen source.

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proposed mechanism



Key Words

nitrogen heterocycles, 1,2-oxazetidines, tert-butyl hydroperoxide, multicomponent reactions


ID: J54-Y2017