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Issue 27, 2012
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Reactions of 1-alkyl-1,2-diphospholes with 1,3-dipoles: diphenyldiazomethane and nitrones

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Abstract

The reaction of 1-alkyl-1,2-diphosphacyclopenta-2,4-dienes (1-alkyl-1,2-diphospholes) (1) with diphenyldiazomethane proceeds at room temperature via unstable [3+2] cycloadducts to form bicyclic phosphiranes (2). However, 1-alkyl-1,2-diphospholes (1) react with N,alpha-diphenylnitrone or N-tert-butyl-alpha-phenylnitrone depending on the temperature to give either dimers of 1-alkyl-1-oxo-1,2-diphospholes (5) or 1-alkyl-1,7-dioxo-6-azo-1,7-diphospha-bicyclo[3.2.0]hept-2-enes (7) – phosphorus analogues of β-lactams.

Graphical abstract: Reactions of 1-alkyl-1,2-diphospholes with 1,3-dipoles: diphenyldiazomethane and nitrones

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Article information


Submitted
12 Mar 2012
Accepted
15 May 2012
First published
15 May 2012

Org. Biomol. Chem., 2012,10, 5298-5306
Article type
Paper

Reactions of 1-alkyl-1,2-diphospholes with 1,3-dipoles: diphenyldiazomethane and nitrones

A. Zagidullin, Y. Ganushevich, V. Miluykov, D. Krivolapov, O. Kataeva, O. Sinyashin and E. Hey-Hawkins, Org. Biomol. Chem., 2012, 10, 5298
DOI: 10.1039/C2OB25532D

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