Abstract
First-order analysis of the 60 Mc.p.s. proton magnetic resonance spectra of 1α-methoxy-2β-acetoxy-3α-bromocyclohexane, 1α-methoxy-2α-acetoxy-3β-bromocyclohexane, 1α-methoxy-2β-bromo-3α-acetoxycyclohexane, 1α-methoxy-2α-bromo-3β-acetoxycyclohexane, and the corresponding diol diacetates confirmed the stereochemical interrelationships of substituents which were assigned previously on chemical grounds, and demonstrated that the compounds exist in chair conformations. The chemical shifts of the methoxy methyl and acetoxy methyl protons did not provide reliable criteria for the assignment of conformations to these substituents in this series. The coupling constants of the methine protons followed, in general, the pattern predicted by the Karplus equation, and the smaller J2,3 values observed in the cis,trans compounds relative to those in the trans,trans compounds are interpreted mainly on the basis of conformational equilibration, upon which is superimposed a small dihedral angular distortion or a remote substituent orientational effect.
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