Journal of Organic Chemistry

Stereochemistry of. beta.-keto ester and. beta.-keto nitrile alkylations

ME Kuehne

Index: Kuehne,M.E. Journal of Organic Chemistry, 1970 , vol. 35, # 1 p. 171 - 175

Full Text: HTML

Citation Number: 28

Abstract

The methylations of Zcarbomethoxy-and 2-cyano-4-t-butylcyclohexanone gave predominantly axial alkyla-tion products. With 3-carbomethoxy-and 3-oyano-lO-met~ hyl- trans-2-decalones the oppofiite stereochemical result was obtained. While a boat or twist conformation is indicated for the substituted ring product in the former case by nmr and vpc, a chair conformation was found for the nitrile product.