Reaction of Arylmethyl Isocyanides/Arylmethyl-amines with Xanthate Esters: A Facile and Unexpected Synthesis of Carbamothioates

  1. Narasimhamurthy Rajeev,
  2. Toreshettahally R Swaroop,
  3. Seegehalli M Anil,
  4. Kupalli R Kiran,
  5. Chandru Chandru,
  6. Paris E Georghiou,
  7. Ahmad I AlrawashdehORCID Logo,
  8. Shofiur Rahman,
  9. Abdullah Alodhayb,
  10. Kanchugarakoppal S Rangappa and
  11. Maralinganadoddi P SadashivaORCID Logo

Submitting author affiliation: University of Mysore, Mysuru, India

Beilstein Arch. 2019, 201926. doi:10.3762/bxiv.2019.26.v1

Published 21 May 2019

  • Preprint


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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When a peer-reviewed version of this preprint is available in the Beilstein Journals, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

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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