Stereochemical course of the reaction of 2-haloethyl isothiocyanates with nucleophiles. Stereospecific route to 4,5-disubstituted Δ2-thiazolines and thiazolidine-2-thiones

Abstract

Diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes have been prepared. They reacted stereospecifically with CH3Ona, diethylamine, aniline and NaSH to give pure cis or trans-4,5-disubstituted Δ2-thiazolines and thiazolidine-2-thiones whose configuration was determined using the nuclear Overhauser effect. The preponderant conformation of diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes was estimated on the basis of coupling constants of vicinal protons.