130452-67-4Relevant academic research and scientific papers
Mechanism of Photoreduction of Diethyl Benzylidene Malonates by NAD(P)H Model and Comparison with Thermal Reaction
Deng, Gang,Xu, Hui-Jun,Chen, De-Wen
, p. 1133 - 1137 (2007/10/02)
Photoreduction of diethyl benzylidene malonates by NAD(P)H model has been investigated.The reduction of the carbon-carbon bond occurs and is enhanced by electron-withdrawing groups on the benzene ring.Deuteriation experiments in 2H4>methanol showed that hte deuterium which originated from the solvent was mainly incorporated at the β-carbon.The mechanism of photoreduction is discussed in terms of sequential electron-hydrogen atom transfer from NAD(P)H model to the substrate in the solvent cage.On the other hand, thermal reduction of NAD(P)H model with the substrates in methan-2H>-ol and/or 2H4>methanol gave the reduced products with deuterium incorporated at the α-carbon.Reduction of diethyl benzylidene malonates with 2H2>-1-benzyl-1,4-dihydronicotinamide (BNAH) led to the direct transfer of deuterium from C-4 to the β-carbon.These results have been interpreted as support for the direct hydride transfer mechanism.
