Versatile Cycloaddition Reactions of 1-Alkyl-1,2-Diphospholes

Author: Zagidullin Almaz   Ganushevich Yulia   Miluykov Vasili   Sinyashin Oleg   Hey-Hawkins Evamarie  

Publisher: Taylor & Francis Ltd

ISSN: 1042-6507

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Vol.188, Iss.1-3, 2013-01, pp. : 238-242

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Abstract

The reactivity of 1-alkyl-1,2-diphospholes in cycloaddition reactions with dienes, dienophiles or 1,3-dipoles was examined. 1-Alkyl-1,2-diphospholes (2 ) exhibit dual reactivity and act as diene toward maleic acid derivatives or as dienophiles with 2,3-dimethyl-1,3-butadiene. The 1-alkenyl-1,2-diphospholes (4 ) are readily involved in intramolecular [4 + 2] cycloaddition reactions leading to cage phosphines (5 ). Interaction of 1-alkyl-1,2-diphospholes (2) with 1,3-dipolar reagents (diphenyldiazomethane and nitrones) results in formation of the bicyclic phosphiranes (8) and dimers of 1-alkyl-1,2-diphosphole oxides (9) or bicyclic phosphine oxides (10) with a β-lactam moiety depending on temperature.

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