Polar Substituents in Pericyclic Reactions: Mechanistic Course of the 2π + 2π Photocycloaddition of Dimethyl 1,4-Dihydro-1,4-ethenonaphthalene-2,3-dicarboxylate

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Abstract
Deuterium labeling studies are consistent with the initial photochemical 2π + 2π closure of singlet excited dimethyl 1,4-dihydro-1,4-ethenonaphthalene-2,3-dicarboxylate (4) proceeding via bridging between the vinyl and vinyl diester moieties and not via the vinyl–benzo bridging mode favored by Grovenstein and by the Epiotis polar pericyclic theory. The possible involvement of the charge-transfer excited state of 4 in the reaction is discussed.

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