ABSTRACT
The conformations and relative configurations of 20 amines, classified according to the following labeling scheme, were analyzed. Series a comprised compounds derived from N-(1-phenylethyl)cyclohexanamine, b comprised derivatives of N-[1-(naphthalen-2-yl)ethyl]cyclohexanamine, c comprised derivatives of N-(diphenylmethyl)cyclohexanamine, and d comprised derivatives of N-(propan-2-yl)cyclohexanamine. The compounds were labeled as follows: 1 indicates cyclohexanamine, 2 indicates 2-methylcyclohexanamines, 3 indicates 3-methylcyclohexanamines, 4 indicates 4-methylcyclohexanamines, and 5 indicates 4-tert-butylcyclohexanamines. These compounds were prepared without the use of stereoselective induction and, therefore, all expected stereoisomers were observed. Structural assignments were established by (1)H, (13)C, and (15)N NMR.
Subject(s)
Amines/chemistry , Cyclization , Cyclohexanes/chemistry , Magnetic Resonance Spectroscopy/methods , Molecular Conformation , Molecular StructureABSTRACT
The (1)H, (13)C, and (15)N NMR spectra of 5 exocyclic alkenes and 15 different ketimines obtained from cyclohexanone and derivatives using benzyl bromide and primary amines-are analyzed. Relative stereochemical and preferential conformations are determined by analyzing both the homonuclear coupling and the chemical shifts of the protons and carbon atoms in the aliphatic rings, which are directly related to the geometry of the double bond and the steric and electronic effects of the exocyclic group. In addition, the racemic mixture of the N-(4-methylcyclohexylidene)pyridine-3-amine derivative is resolved.
Subject(s)
Cycloparaffins/analysis , Imines/analysis , Nuclear Magnetic Resonance, Biomolecular/methods , Cyclohexanones/chemistry , Models, Molecular , Molecular Structure , Reference Standards , Sensitivity and Specificity , StereoisomerismABSTRACT
The configurational properties of a series of cyclohexylidene imines are discussed on the basis of their 1H, 13C and 15N NMR spectral data.
