Mechanistic and synthetic aspects of amine oxidations promoted by 3-methyl-5-ethyllumiflavinium perchlorate

Article abstract of DOI:10.1016/S0040-4020(97)00206-8

Preparative and kinetic aspects of the chemistry of 3-methyl-5-ethyllumiflavinium perchlorate (1) with primary and secondary amines have been investigated. Reactions of! with primary and secondary amines leads to rapid production of modestly stable C4a-adducts. The rates of these processes, determined by stopped-flow kinetic methods, parallel amine nucleophilicities. The C4a-adducts undergo benzylamine promoted elimination reactions to produce N-benzylaldimine products with rates that parallel reactivity profiles expected for E₂-elimination processes. Finally, flavinium salt 1 serves as a catalyst for oxidations of primary and secondary amines under aerobic conditions.