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Generation of Nitrile Oxides from Oximes Using t-BuOI and Their Cycloaddition

Satoshi Minakata*, Sota Okumura, Toshiki Nagamachi and Youhei Takeda

*Department of Applied Chemistry and Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Email: minakatachem.eng.osaka-u.ac.jp

S. Minakata, S. Okumura, T. Nagamachi, Y. Takeda, Org. Lett., 2011, 13, 2966-2969.

DOI: 10.1021/ol2010616 (free Supporting Information)



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Abstract

tert-Butyl hypoiodite (t-BuOI), generated in situ from t-BuOCl and NaI, is a powerful reagent for the cycloaddition of oximes to alkenes or alkynes, leading to various isoxazolines or isoxazoles under mild conditions.

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mechanism for formation of nitril oxides



Key Words

2-isoxyzolines, 1,3-dipolar cycloaddition


ID: J54-Y2011-1650