THIOLYSIS AND HYDROLYSIS OF IMINO AND IMINIUM TRIFLATES - SYNTHESIS OF SECONDARY AND TERTIARY THIOAMIDES AND O-18-LABELED AMIDES

Authors
CHARETTE AB CHUA P
Citation
Ab. Charette et P. Chua, THIOLYSIS AND HYDROLYSIS OF IMINO AND IMINIUM TRIFLATES - SYNTHESIS OF SECONDARY AND TERTIARY THIOAMIDES AND O-18-LABELED AMIDES, Tetrahedron letters, 39(3-4), 1998, pp. 245-248
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
3-4
Year of publication
1998
Pages
245 - 248
Database
ISI
SICI code
0040-4039(1998)39:3-4<245:TAHOIA>2.0.ZU;2-T
Abstract
Secondary and tertiary amides were treated with trifluoromethanesulfon ic (triflic) anhydride in the presence of pyridine at low temperatures to generate imino and iminium triflates. Subsequent treatment with hy drogen sulfide immediately gave rise to the corresponding thioamide in good to excellent yields at low temperature. Alternatively, treatment with stoichiometric amounts of O-18-labeled water produced the O-18-l abeled amide. (C) 1997 Elsevier Science Ltd. All rights reserved.