Conformational equilibria in cis-C-methyldecahydroquinolines: studies at low temperature using 13C and 1H magnetic resonance spectroscopy

Abstract

A number of cis- and trans-methyldecahydroquinolines, substituted at C-2, -3, -4, -4a, and -8a, have been synthesised and their preferred conformations established by variable temperature ¹³C and ¹H n.m.r. spectroscopy. The conformational preference, for the equatorial orientation, of a methyl at C-4 of cis-decahydroquinoline, is similar to that of a methyl in cyclohexane, whereas that of a methyl at C-2 or -8a is considerably greater.