Beilstein J. Org. Chem.2020,16, 159–167, doi:10.3762/bjoc.16.18
Interface Sciences, Department, of Physics and Astronomy, College of Science, King Saudi University, Riyadh 11451, Saudi Arabia Department of Physics, National Institute of Engineering, Mysuru, Karnataka 570 008, India 10.3762/bjoc.16.18 Abstract An unexpected formation of carbamothioates by a sodium
hydride-mediated reaction of arylmethyl isocyanides with xanthate esters in DMF is reported. The products thus obtained were compared with the carbamothioates obtained by the sodium hydride-mediated condensation of the corresponding benzylamines and xanthate esters in DMF. To account for these unexpected
reactions, a mechanism is proposed in which the key steps are supported by quantum chemical calculations.
Keywords: benzylamines; carbamothioates; density functional theory; intrinsic reaction coordinate analysis; isocyanides; sodium hydride; xanthate esters; Introduction
Carbamothioates (thiocarbamates
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Graphical Abstract
Scheme 1:
Synthesis of carbamothioates from xanthate esters and benzyl isocyanides.