N-1,N-10-ethylene-bridged high-potential flavins: synthesis, characterization, and reactivity

Citation
Ws. Li et al., N-1,N-10-ethylene-bridged high-potential flavins: synthesis, characterization, and reactivity, TETRAHEDRON, 57(21), 2001, pp. 4507-4522
Citations number
53
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
0040-4020 → ACNP
Volume
57
Issue
21
Year of publication
2001
Pages
4507 - 4522
Database
ISI
SICI code
0040-4020(20010521)57:21<4507:NHFSC>2.0.ZU;2-H
Abstract
N-1,N-10-Ethyleneisoalloxazinium chloride and its 8-Cl-, 7-CF3-, and 3-CH3- 7-CF3-substituted analogs were synthesized for the purpose of exhibiting th ermal reactivity with organic substrates. The new flavins were characterize d spectroscopically and electrochemically, and were found to react with ami nes, thiols, and phenylhydrazine, the latter case exhibiting catalytic aero bic recycling. Reactions of aliphatic benzylic and cyclopropyl amines with the 7-CF3 analog were also compared to their oxidations by tris(phenanthrol ine)iron(III). All reactions of the flavinium salts appear to occur through heterolytic rather than homolytic mechanisms. (C) 2001 Elsevier Science Lt d. All rights reserved.