Abstract
Abstract Thioacetamide, thioacetamide S-oxide (1), and thiopivalamide S-oxide (8) were oxidized with H2O2 in H2 18O to generate the corresponding amides with at least 50% 18O incorporation; hydrolysis of the S-oxides to the amides or 18O exchange with the amides occurs much more slowly. When 1 and trifluorothioacetamide (6) were oxidized with three and four equivalents of H2O2, respectively, in the presence of benzylamine, N-acetylbemylamine (5) and N-benzyltrifluoroacetamide (7) were isolated in respective yields of 17% and 37%. These results are interpreted as evidence for an oxidative desulfurization mechanism involving nucleophilic attack at the carbon atom of an S,S-dioxide or trioxide intermediate as the major pathway; a minor pathway may involve the intermediacy of an oxathiirane S -oxide (3) or dioxide (4) species. Understanding is added to the behavior of S-oxides in aqueous solution, as well as to thermal stability in deuterochloroform. Also reported are studies of the preparation and properties...
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
