Open AccessCYCLOHEXANE COMPOUNDS: IV. NUCLEAR MAGNETIC RESONANCE SPECTRA OF SOME DERIVATIVES OF THE STEREOISOMERIC 3-AMINO-1,2-CYCLOHEXANEDIOLS
Author(s) -
F. A. L. Anet,
R. A. B. Bannard,
L. D. Hall
Publication year - 1963
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v63-338
Subject(s) - chemistry , chemical shift , chloroform , coupling constant , alkoxy group , acetic anhydride , derivative (finance) , cyclohexane , diacetyl , stereochemistry , computational chemistry , medicinal chemistry , alkyl , organic chemistry , physics , particle physics , catalysis , financial economics , economics
The n.m.r. spectra of 1α-methoxy-2β-hydroxy-3α-aminocyclohexane, 1α-methoxy-2α-hydroxy-3β-aminocyclohexane, their N-acetyl and O,N-diacetyl derivatives, ethoxy analogues, and 3α-amino-1α,2β-cyclohexanediol and 3β-amino-1α,2β-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 1α-alkoxy-2α-hydroxy-3β-aminocyclohexanes with acetic anhydride gave both the O,N-diacetyl derivative and the O,N,N-triacetyl derivative.