Evidence for a concerted [4 + 1]- cycloaddition between electron-rich carbenes and electron-deficient dienes.

Org Lett

Département de Chimie, Université de Sherbrooke, 2500 Boul. Université, Sherbrooke, QC, Canada J1K 2R1.

Published: December 2007

Results from the thermal reactions of deuterated dienes 12-15 provide evidence of the concertedness of the [4 + 1]-cycloaddition between dimethoxycarbene and electron-deficient dienes. Other evidence suggests that the main pathway is a concerted [4 + 1]-cycloaddition rather than a cyclopropanation followed by a vinylcyclopropane rearrangement. Ionic pathways can become competitive when steric or geometrical constraints are present.

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Source
http://dx.doi.org/10.1021/ol702172tDOI Listing

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