The Journal of Organic Chemistry

Autoxidation of 2-cyano-3, 3-disubstituted carboxylate anions. Synthesis of 3, 3-disubstituted 2-oxocarboxylates

N Rabjohn, CA Harbert

Index: Rabjohn,N.; Harbert,C.A. Journal of Organic Chemistry, 1970 , vol. 35, # 10 p. 3240 - 3243

Full Text: HTML

Citation Number: 10

Abstract

Ethyl 3, 3-dipentyl-2-oxooctanoate, Sa, was isolated in low yields when oxygen was passed into the Grignard complex, 1, R1= R,= Rs= CsHll, obtained from the conjugate addition of pentylmagnesium bromide to ethyl 2-cyan0-3-pentyl-Z-octenoate. The extension of this base- catalyzed autoxidation to ethyl 2-cyano 3, 3-disubstituted carboxylates, 2, in polar solvents was found to afford good yields of 2-oxo esters, 3. It was shown that the nitrile group of 2 is ...