Collect. Czech. Chem. Commun. 1981, 46, 717-728

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

Ladislav Kniežoa, Pavol Kristiana, Miloš Buděšínskýb and Katarína Havrilováa

a Department of Organic Chemistry, P. J. Šafárik University, 041 67 Košice
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


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.