Beilstein J. Org. Chem.2020,16, 159–167, doi:10.3762/bjoc.16.18
hydride-mediated reaction of arylmethyl isocyanides with xanthateesters 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 xanthateesters 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; xanthateesters; Introduction
Carbamothioates (thiocarbamates
of xanthateesters with amines [18]. Furthermore, many methods have also been reported for the synthesis of cyclic thiocarbamates, and these include reactions of isothiocyanates with aldehydes in the presence of organocatalysts [19][20], reactions of vicinal diols with potassium thiocyanate [21
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Graphical Abstract
Scheme 1:
Synthesis of carbamothioates from xanthate esters and benzyl isocyanides.