Journal of the American Chemical Society

Regioselectivity in the addition of singlet and triplet carbenes to 1, 1-dimethylallene. A probe for carbene multiplicity

X Creary

Index: Creary, Xavier Journal of the American Chemical Society, 1980 , vol. 102, # 5 p. 1611 - 1618

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Citation Number: 39

Abstract

Abstract: Singlet carbenes add preferentially to the more substituted bond of 1, I- dimethylallene (1). to give methylenecyclopropanes 3 as the major product. In contrast, many triplet carbenes add with differing regioselectivity, giving the thermodynamically preferred isopropylidenecyclopropanes, 10. A mechanism involving an intermediate trimethylenemethane, 8, has been suggested for this product. This regioselectivity probe ...