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Visible-Light-Induced Aza-Pinacol Rearrangement: Ring Expansion of Alkylidenecyclopropanes

Wen-Deng Liu, Guo-Qiang Xu, Xiu-Qin Hu and Peng-Fei Xu*

*State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China, Email: xupflzu.edu.cn

W.-D. Liu, G.-Q. Xu, X.-Q. Hu, P.-F. Xu, Org. Lett., 2017, 19, 6288-6291.

DOI: 10.1021/acs.orglett.7b02989 (free Supporting Information)


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Abstract

In a visible-light-induced aza-pinacol rearrangement, the addition of the N-centered radical to the C=C bond of alkylidenecyclopropanes provides various cyclobutanimines in good yields under mild reaction conditions. Ring expansion delivers γ-butyrolactones.

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proposed mechanism



Key Words

pinacol rearrangement, cylobutanones


ID: J54-Y2017