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

Abstract

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.

Keywords

• Photo-induced electron transfer reaction
• 2-Phenylthioalcohol
• Deoxyazasugars
• Thiophenol
• Scavenger
• Ab initio calculation