Mechanism of electron transfer oxidation of 4-substituted 1-benzyl-1,4-dihydronicotinamides

Article abstract of DOI:10.1246/cl.1996.1103

Electron transfer oxidation of variously 4-substituted 1-benzyl-1,4-dihydronicotinamides (RBNAH) by [Fe(phen)₃]³⁺ (phen = 1,10-phenanthroline) results in formation of RBNAH^?+, followed by cleavage of the C(4)-H or C(4)-C bond of RBNAH^?+ depending on the substituent R. In particular, the C(4)-C bond cleavage of t-BuBNAH^?+ yields exclusively BNA⁺ and tert-butyl radical (t-Bu^?) which is detected by applying a rapid mixing flow electron spin resonance (ESR) technique.