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Single-Step Process for the Reductive Deoxygenation of Unhindered Alcohols

Andrew G. Myers,* Mohammad Movassaghi and Bin Zheng

*Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, Email:

A. G. Myers, M. Movassaghi, B. Zheng, J. Am. Chem. Soc., 1997, 119, 8572-8573.

DOI: 10.1021/ja971768v

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Mitsunobu displacement of an alcohol with o-nitrobenzenesulfonylhydrazide followed by in situ elimination of o-nitrobenzenesulfinic acid generates monoalkyl diazenes, which decompose by a free-radical mechanism to form deoxygenated products.

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proposed reaction pathway

Key Words

deoxygenations, o-nitrobenzenesulfonylhydrazide, Mitsunobu reaction

ID: J48-Y1997-760