Stereochemistry of sulphur organic compounds. Part 11. A conformational study of some 2-thio-derivatives of N-phenyl-1-phenylethylamine

Abstract

The syntheses and a conformational study of N-phenyl-2-Y-1-phenylethylamine [Y = SCH₃, SOCH₃(two diastereoisomers), SO₂CH₃, and ⁺S(CH₃)₂] are reported. Conformational preferences have been established from changes in the vicinal coupling constants induced by protonation at the amine nitrogen. This determines the electrostatic character of the interactions between the two heteroatoms functions. In addition, the configurational assignment for diastereoisomeric sulphoxides is also reported.