78962-00-2Relevant academic research and scientific papers
Synthesis and Conformational Analysis of Substituted 4-Aminothianes
Subramanian, Pullachipatti K.,Ramalingam, Kondareddiar,Satyamurthy, Nagichettiar,Berlin, K. Darrell
, p. 4376 - 4383 (2007/10/02)
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.
