The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates.
Narasimhamurthy RajeevToreshettahally R SwaroopAhmad I AlrawashdehShofiur RahmanAbdullah AlodhaybSeegehalli M AnilKuppalli R Kirannull ChandraParis E GeorghiouKanchugarakoppal S RangappaMaralinganadoddi P SadashivaPublished in: Beilstein journal of organic chemistry (2020)
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.