Jong Man Kim, M. A. Bogdan, P. Mariano
Nov 1, 1993
Citations
0
Influential Citations
72
Citations
Quality indicators
Journal
Journal of the American Chemical Society
Abstract
An investigation designed to probe flavin-promoted oxidative deaminations of amines is described. 3-Methyllumiflavin (3MLF) has been found to promote clean conversion of benzylamine to N-benzylbenzaldimine under acid (HCl or MgCl 2 ) catalyzed, thermal (80 o C) conditions. The reaction is subject to multiple turnover. Amine structure (1 o >2 o >3 o ) and α-electrofugal group leaving ability (TMS + >H + ) are found to influence reactivity. In addition, the internal d-isotope efeect measured for the ground-state reaction by using PhCHDNH 2 is found to be 4.3, a value greatly different from the 1.6 measured for the excited-state (SET) reaction run under nearly identical (20 o C rather than 80 o C) conditions