Tetrahedron

Stereochemical studies—XXVI: Conformational Equilibria of ketals of 2-substituted cyclohexanones

IG Mursakulov, MM Guseinov, NK Kasumov, NS Zefirov…

Index: Mursakulov, Ismail G.; Guseinov, M. M.; Kasumov, N. K.; Zefirov, Nikolai S.; Samoshin, V. V.; Chalenko, E. G. Tetrahedron, 1982 , vol. 38, # 14 p. 2213 - 2220

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Citation Number: 10

Abstract

The position of the conformational equilibria in a series of 2-substituted cyclohexanone ketals have been determined by 1H NMR. For the ethylene ketals 6 the equatorial conformer has been found to be enthalpically preferred. The other ketal system (5, 7–9), in contrast, display predominance of axial conformers. The reasons for this behavior are discussed in terms of rotameric conformations of acetal chains.