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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.
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Reference：
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem