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Reactions of 1-alkyl-1,2-diphospholes With 1,3-dipoles: Diphenyldiazomethane and Nitrones

Almaz Zagidullin, Yulia Ganushevich, Vasili Miluykov, Dmitry Krivolapov, Olga Kataeva, Oleg Sinyashin, Evamarie Hey-Hawkins

Org Biomol Chem. 2012 Jul 21;10(27):5298-306.

PMID: 22684400

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP598209 1,2-Dibromo-1-chloroethane 1,2-Dibromo-1-chloroethane 598-20-9 Price
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