Canadian Journal of Chemistry

Regioselectivity of metal hydride reductions of unsymmetrically substituted cyclic anhydrides. systems where" steric hindrance along the preferred reaction path" …

MM Kayser, P Morand

Index: Kayser, Margaret M.; Morand, Peter Canadian Journal of Chemistry, 1980 , vol. 58, p. 2484 - 2490

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Citation Number: 29

Abstract

Metal hydride reductions of planar cyclic anhydrides such as methylmaleic or 3-substituted phthalic anhydrides occur preferentially at the sterically more hindered carbonyl function. This regioselectivity cannot be rationalized in terms of" the most favourable pathway for non- perpendicular attack by a nucleophile" since both carbonyl groups present are equally accessible to non-perpendicular approach. A study which takes into account the alkaline ...