Stereochemical Implications of Hindered Rotation about the S-N Bond in Bis(dialkylamino)mono- and di-sulfides.

Abstract

Bis ( dialkylamino )mono- and di-sulfides were prepared and characterized by NMR, IR, and mass spectroscopy and, in some cases, also by elemental analysis. Variable temperature PMR studies of these compounds indicate that, at low temperatures, the substituents on nitrogen exist in diastereotopic environments. The PMR spectra further suggest that, in the case of the disulfides, the stereo­chemistry of the N-S-S-N moiety of the molecules is not coplanar but "gauche". At room temperature, rotation about the S-S bond appears to be slow, and the barriers observed at low temperatures are tentatively assigned to hindered S-N rotation.