GENERATION OF N-ACYL IMINIUM IONS FROM IONIZATION-REARRANGEMENT REACTIONS OF N-TRIFLYLOXY AMIDES

Authors
HOFFMAN RV NAYYAR NK SHANKWEILER JM KLINEKOLE BW
Citation
Rv. Hoffman et al., GENERATION OF N-ACYL IMINIUM IONS FROM IONIZATION-REARRANGEMENT REACTIONS OF N-TRIFLYLOXY AMIDES, Tetrahedron letters, 35(20), 1994, pp. 3231-3234
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
20
Year of publication
1994
Pages
3231 - 3234
Database
ISI
SICI code
0040-4039(1994)35:20<3231:GONIIF>2.0.ZU;2-B
Abstract
N-Triflyloxy amides undergo ionization in refluxing isopropanol to giv e N-acyliminium ions which can be trapped by addition of allyltrimethy lsilane to the reaction mixture. Alternatively they can be converted t o N-(isopropoxy)alkyl amides and then back to N-acyliminium ions under a variety of conditions.