THE DEALKYLATION OF TERTIARY ALIPHATIC-AMINES WITH PHENYL CHLOROTHIONOFORMATE

Authors
MILLAN DS PRAGER RH
Citation
Ds. Millan et Rh. Prager, THE DEALKYLATION OF TERTIARY ALIPHATIC-AMINES WITH PHENYL CHLOROTHIONOFORMATE, Tetrahedron letters, 39(24), 1998, pp. 4387-4390
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
24
Year of publication
1998
Pages
4387 - 4390
Database
ISI
SICI code
0040-4039(1998)39:24<4387:TDOTAW>2.0.ZU;2-C
Abstract
Phenyl chlorothionoformate reacts rapidly with aliphatic amines at 20 degrees C to give a thiourethane and an alkyl chloride. The urethanes are readily converted to the secondary amine salt by reaction with dim ethyl sulfate, followed by hydrolysis with water. Rates of reaction, a nd alkyl group cleavage selectivity, are comparable to those reported for 1-chloroethyl chloroformate. (C) 1998 Elsevier Science Ltd. All ri ghts reserved.