On the Selectivity of the Cleavage of 2‐Substituted Aziridines in the Synthesis of Thiazolidines | Zendy

Barbry Didier | Zendy; Couturier Daniel | Zendy

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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.

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