Hetero-Diels−Alder Reactions of 2H-Phospholes with Aldehydes
- 4 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (7) , 2803-2806
- https://doi.org/10.1021/jo020720j
Abstract
Transient 2-phenyl-3,4-dimethyl-5H-phosphole reacts at 150 degrees C with aldehydes RCH=O to give the corresponding [4 + 2] P-O cycloadducts with endo- (major) and exo-R-substituents. The cycloaddition with alpha,beta-unsaturated aldehydes takes place both at the C=O (major) and C=C bonds. Upon heating under reduced pressure, the benzaldehyde cycloadduct dissociates to give back the 2H-phosphole, which either dimerizes, is trapped by diphenylacetylene, or is deprotonated by (t)BuOK.Keywords
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