An unexpected formation of carbamothioates by the reaction of arylmethyl isocyanides with xanthate esters in the presence of sodium hydride is reported. The products thus obtained were compared with carbamothioates obtained by the condensation of the corresponding benzylamines with xanthate esters in the presence of sodium hydride in DMF. A mechanism which is substantiated by DFT calculations to account for the unexpected reactions is proposed.
Keywords: Xanthate esters; Isocyanides; Benzylamines; Carbamothioates; Sodium hydride; Density Functional Theory, Intrinsic Reaction Coordinate Analysis
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Rajeev, N.; Swaroop, T. R.; Anil, S. M.; Kiran, K. R.; Chandru, C.; Georghiou, P. E.; Alrawashdeh, A. I.; Rahman, S.; Alodhayb, A.; Rangappa, K. S.; Sadashiva, M. P. Beilstein Arch. 2019, 201926. doi:10.3762/bxiv.2019.26.v1
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