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

Narasimhamurthy Rajeev; Toreshettahally R Swaroop; Seegehalli M Anil; Kupalli R Kiran; Chandru Chandru; Paris E Georghiou; Ahmad I Alrawashdeh; Shofiur Rahman; Abdullah Alodhayb; Kanchugarakoppal S Rangappa; Maralinganadoddi P Sadashiva

doi:10.3762/bxiv.2019.26.v1

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

Narasimhamurthy Rajeev ,
Toreshettahally R Swaroop ,
Seegehalli M Anil ,
Kupalli R Kiran ,
Chandru Chandru ,
Paris E Georghiou ,
Ahmad I Alrawashdeh ,
Shofiur Rahman ,
Abdullah Alodhayb ,
Kanchugarakoppal S Rangappa and
Maralinganadoddi P Sadashiva

Submitting author affiliation:

University of Mysore, Mysuru, India

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

Published 21 May 2019

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Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

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, 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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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)