The Diels-Alder additions of phenylcyclopentadienes: Tests for the PMO theory and the diradicaloid model

Abstract The cycloaddition of phenylcyclopentadiene 1 generated in situ through dehydration of 3-phenylcyclopenten-3-ol 2 with a-thioacrylonitriles 3 (captodative dienophiles) exhibit high regio and stereoselectivity. The reactions provide access to 2-phenylnorbornene derivatives.