S. Denmark, M. Dappen, Nancy L. Sear
Apr 1, 1990
Citations
0
Influential Citations
66
Citations
Journal
Journal of the American Chemical Society
Abstract
A series of trans-3-alkyl-2-chlorocyclohexanones, (methyl, ethyl, isopropyl, and tert-butyl), have been prepared and shown to exist predominantly in the diequatorial chair conformation except the tert-butyl derivative which prefers a twist-boat. Formation of the oximes and various oxime derivatives (methyloxime, silyloxime) results in a remarkable conformational inversion for the methyl, ethyl, and isopropyl systems. By analysis of vicinal interproton coupling constants it is believed that these compounds exist predominantly in the diaxial chair conformation