Abstract
A series of compounds o-bromomethylbenzylidene-malononitrile (1), dimethyl o-bromomethyl-benzylidenemalonate (2) and mthyl alpha-cyano-o-bromomethylcinnamate (3) were reduced in the dark and under irradiation by an NAP(P)H model, 1-benzyl-1,4-dihydronicotinamide (BNAH). Two different mechanisms were found, i.e. one-step hydride transfer (polar pathway) and multi-step sequence initiated by single electron transfer (SET pathway). The effect of electron-withdrawing groups on the reactivity of the Substrates were discussed in terms of Hammett substituent constants, C-13 NMR chemical shift values and cyclic voltammetric redox potentials, mid their correlations. (C) 2002 Elsevier Science Ltd. All rights reserved.
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