Regioselectivity in cycloadditions of singlet 2-methylenecyclopenta-1, 3-diyl species

RK Siemionko, JA Berson

Index: Siemionko,R.K.; Berson,J.A. Journal of the American Chemical Society, 1980 , vol. 102, p. 3870

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Citation Number: 24

Abstract

Abstract: The regioselectivity for fused adduct in the cycloaddition of singlet 2- methylenecyclopenta-1, 3-diyls to olefins can be explained either as an orbital overlap effect in a reaction of a bisected singlet trimethylenemethane (TMM) or as an orbital symmetry effect in a reaction of a planar singlet TMM. The first hypothesis predicts the same regioselectivity in 1, 2 and 1, 4 cycloadditions to conjugated dienes (fused adducts), but ...

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