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P–C Bond Cleavage by Hydroxyl Function during the Addition of Tris(2‐pyridyl)phosphine to Cyanopropargylic Alcohols in Water

P–C Bond Cleavage by Hydroxyl Function during the Addition of Tris(2‐pyridyl)phosphine to... ABSTRACT The addition of tris(2‐pyridyl)phosphine to tertiary cyanopropargylic alсоhols in water (room temperature, no catalyst, 5 h) is accompanied by elimination of pyridine to give cyanoallyldipyridylphosphinates of E‐configuration in 60–73% yield, thus indicating the oxygen insertion of the hydroxyl group into the PC bond of the intermediate (Z)‐alkenyldipyridylphosphine oxide. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

P–C Bond Cleavage by Hydroxyl Function during the Addition of Tris(2‐pyridyl)phosphine to Cyanopropargylic Alcohols in Water

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References (31)

Publisher
Wiley
Copyright
Copyright © 2015 Wiley Periodicals, Inc.
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.21253
Publisher site
See Article on Publisher Site

Abstract

ABSTRACT The addition of tris(2‐pyridyl)phosphine to tertiary cyanopropargylic alсоhols in water (room temperature, no catalyst, 5 h) is accompanied by elimination of pyridine to give cyanoallyldipyridylphosphinates of E‐configuration in 60–73% yield, thus indicating the oxygen insertion of the hydroxyl group into the PC bond of the intermediate (Z)‐alkenyldipyridylphosphine oxide.

Journal

Heteroatom ChemistryWiley

Published: May 1, 2015

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