Conformational analysis of 3α-halogenotropanes

Abstract

The conformation of 3α-chloro- and 3α-bromo-tropane was studied by means of dipole moments and n.m.r. spectroscopy. The results indicate that the conformation of the N-methyl group is an equilibrium between the equatorial and axial positions and that the 3α-substituent gives rise to a distortion of the tropane skeleton. The synthesis of 3α-bromotropane is described; two methods were used, both stereospecific.