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On the Selectivity of the Cleavage of 2‐Substituted Aziridines in the Synthesis of Thiazolidines
Author(s) -
Barbry Didier,
Couturier Daniel
Publication year - 1987
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19871200632
Subject(s) - chemistry , aziridine , thiazolidine , cleavage (geology) , selectivity , sulfide , ring (chemistry) , hydrogen sulfide , medicinal chemistry , stereochemistry , organic chemistry , catalysis , sulfur , geotechnical engineering , fracture (geology) , engineering
2‐Alkylaziridines react with carbonyl compounds in the presence of hydrogen sulfide to give regioselectively 4‐alkylthiazolidines 1 . With 2‐phenylaziridine 4‐phenyl‐ ( 1d ) and 5‐phenyl‐thiazolidine ( 2d ) are obtained, the latter in larger amounts. This result is rationalized on the basis of pseudoconjugation between the phenyl and aziridine ring.