Reactions of 1-alkyl-1,2-diphospholes with 1,3-dipoles: diphenyldiazomethane and nitrones.
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.
A. E. Arbuzov Institute of Organic and Physical Chemistry Russian Academy of Sciences, Arbuzov Str., 8, 420088 Kazan, Russia.
Almaz
A
Zagidullin
Yulia
Y
Ganushevich
Vasili
V
Miluykov
Dmitry
D
Krivolapov
Olga
O
Kataeva
Oleg
O
Sinyashin
Evamarie
E
Hey-Hawkins
D000478:Alkylation; D001391:Azo Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*
D001391:Azo Compounds; D009589:Nitrogen Oxides; D009943:Organophosphorus Compounds; C532721:diphenyldiazomethane; C015388:nitrones