TY - JOUR A1 - Rajeev, Narasimhamurthy A1 - Swaroop, Toreshettahally R. A1 - Alrawashdeh, Ahmad I. A1 - Rahman, Shofiur A1 - Alodhayb, Abdullah A1 - Anil, Seegehalli M. A1 - Kiran, Kuppalli R. A1 - Chandra, A1 - Georghiou, Paris E. A1 - Rangappa, Kanchugarakoppal S. A1 - Sadashiva, Maralinganadoddi P. T1 - The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates JF - Beilstein Journal of Organic Chemistry PY - 2020/// VL - 16 SP - 159 EP - 167 SN - 1860-5397 DO - 10.3762/bjoc.16.18 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.16.18 KW - benzylamines KW - carbamothioates KW - density functional theory KW - intrinsic reaction coordinate analysis KW - isocyanides KW - sodium hydride KW - xanthate esters N2 - 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. ER -