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The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates
Journal article   Open access  Peer reviewed

The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

Narasimhamurthy Rajeev, Toreshettahally R. Swaroop, Ahmad Alrawashdeh, Shofiur Rahman, Abdullah Alodhayb, Seegehalli M. Anil, Kuppalli R. Kiran, Chandra, Paris E. Georghiou, Kanchugarakoppal S. Rangappa, …
Beilstein journal of organic chemistry, Vol.16(1), pp.159-167
03/02/2020
DOI: https://doi.org/10.3762/bjoc.16.18
PMCID: PMC7034244
PMID: 32117472

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
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.
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https://doi.org/10.3762/bjoc.16.18View
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