CYCLOHEXANE COMPOUNDS. IV. NUCLEAR MAGNETIC RESONANCE SPECTRA OF SOME DERIVATIVES OF THE STEREOISOMERIC 3-AMINO-1,2CYCLOHEXANEDIOLS,
Abstract
The n.m.r. spectra of 1 alpha-methoxy-2 beta-hydroxy3 alpha-aminocyclohexane, 1 alpha-methoxy-2 alphahydroxy-3 beta-aminocyclohexane, their N-acetyl and O,N-diacetyl derivatives, ethoxy analogues, and 3 alphaamino-1 alpha, 2 beta-cyclohexanediol and 3 beta-amino1 alpha, 2 alpha-cyclohexanediol triacetates were measured in chloroform solution. From the chemical shifts of the O- and/or N-acetyl methyl protons it was possible to assign conformations to all the substituted derivatives and in most cases the assignments thus made were confirmed by first-order analysis of the multiplet pattern from the methine protons. In all cases, the conformations found were those predicted on simple conformational grounds and no evidence for a conformational equilibrium at room temperature was obtained from the coupling constants. In general, the coupling constants for the methine protons followed the pattern predicted by the Karplus equation. Acetylation of the 1 alphaalkoxy-2 alpha-hydroxy-3 beta-aminocyclohexanes with acetic anhydride gave both the O,N-diacetyl derivative and the O,N,N-triacetyl derivative. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Apr 29, 1963
- Accession Number
- AD0617504
Entities
People
- F. A. L. Anet
- L. D. Hall
- R. A. B. Bannard