Synthesis and Conformational Analysis of Substituted 4-Aminothianes

Article abstract of DOI:10.1021/jo00335a011

Reductions of substituted 4-thianone oximes by LiAlH4 gave a mixture of epimeric 4-aminothianes.Separation of the epimeric mixture was achieved via column chromatography over neutral alumina.Independent syntheses of these amines by a stereospecific route starting from the tosylate of the corresponding 4-thianols that reacted with sodium azide in DMF followed by reduction of the azide with LiAlH4 provided structure proofs for the amines.N-Acetyl derivatives were also prepared from the aminothianes.Conformational analysis of the amines was performed via an inspection of the (1)H and (13)C NMR spectra.These spectral data suggested t wist conformations for 2,2-dimethyl-trans-6-phenyl-r-4-aminothiane and 2,2-dimethyl-trans-6-p-chlorophenyl-r-4-aminothiane.