Attack of dichlorocarbene on dialkylmercurials. Studies of the stereochemistry and mechanism of insertion into the. beta.-carbon-hydrogen bond

JA Landgrebe, DE Thurman

Index: Landgrebe,J.A.; Thurman,D.E. Journal of the American Chemical Society, 1969 , vol. 91, p. 1759 - 1766

Full Text: HTML

Citation Number: 9

Abstract

Abstract: The attack of dichlorocarbene on dialkylmercurials in which the alkyl function was ethyl, isopropyl, n-propyl, sec-butyl, n-butyl, isobutyl, 2-methylbutyl, n-amyl, isoamyl, cyclohexylmethyl, and cyclopropyl was carried out with the result that the ratio of@-CH to C- Hg insertion increased from 0 to 9 as the 0-CH bond went from primary to tertiary. In two individual cases small amounts of products were isolated which corresponded to bis-/3- ...