The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives

This paper describes the effect of thiophenol concentration on photochemical rearrangement of 2-phenylthio-3-aminocyclohexanols to the corresponding protected aminoaldehydes. The obtained aminoaldehyde is in equilibrium with its corresponding deoxyazasugar. The latter could be converted to the corresponding dehydropiperidine with a good yield in the same reaction media by controlling the thiophenol concentration. Also a proposed mechanism for this one pot transformation is reported.