Versatile Cycloaddition Reactions of 1-Alkyl-1,2-Diphospholes |
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| Authors: | Almaz Zagidullin Yulia Ganushevich Vasili Miluykov Oleg Sinyashin Evamarie Hey-Hawkins |
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| Affiliation: | 1. A. E. Arbuzov Institute of Organic and Physical Chemistry of the Russian Academy of Sciences , Kazan , Russia;2. Institut für Anorganische Chemie, Universit?t Leipzig , Leipzig , Germany |
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| Abstract: | 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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| Keywords: | Polycyclic phosphines 1-alkyl-1,2-diphospholes cycloaddition reactions phosphorus heterocycles |
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