Reactions of 1-alkyl-1,2-diphospholes with 1,3-dipoles: diphenyldiazomethane and nitrones |
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Authors: | Zagidullin Almaz Ganushevich Yulia Miluykov Vasili Krivolapov Dmitry Kataeva Olga Sinyashin Oleg Hey-Hawkins Evamarie |
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Institution: | A. E. Arbuzov Institute of Organic and Physical Chemistry Russian Academy of Sciences, Arbuzov Str., 8, 420088 Kazan, Russia. |
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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-bicyclo3.2.0]hept-2-enes (7) - phosphorus analogues of β-lactams. |
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