Stereochemical course of the reaction of 2-haloethyl isothiocyanates with nucleophiles. Stereospecific route to 4,5-disubstituted Δ2-thiazolines and thiazolidine-2-thiones
1981 ◽
Vol 46
(3)
◽
pp. 717-728
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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.
1980 ◽
Vol 35
(3)
◽
pp. 282-296
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1980 ◽
Vol 58
(12)
◽
pp. 1206-1210
◽
2000 ◽
Vol 54
(4)
◽
pp. 235-248
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Keyword(s):
1998 ◽
Vol 38
(3)
◽
pp. 339-354
◽
1990 ◽
Vol 55
(4)
◽
pp. 1106-1111
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