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

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

doi:10.3762/bjoc.16.18

Beilstein Journal of Organic Chemistry (Feb 2020)

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

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

Affiliations

Narasimhamurthy Rajeev: Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka 570 006, India
Toreshettahally R. Swaroop: Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka 570 006, India
Ahmad I. Alrawashdeh: Department of Chemistry, Memorial University of Newfoundland, St. John’s, Newfoundland and Labrador A1B3X7, Canada
Shofiur Rahman: Department of Chemistry, Memorial University of Newfoundland, St. John’s, Newfoundland and Labrador A1B3X7, Canada
Abdullah Alodhayb: Aramco Laboratory for Applied Sensing Research, King Abdullah Institute for Nanotechnology, King Saudi University, Riyadh, Saudi Arabia
Seegehalli M. Anil: Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka 570 006, India
Kuppalli R. Kiran: Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka 570 006, India
Chandra: Department of Physics, National Institute of Engineering, Mysuru, Karnataka 570 008, India
Paris E. Georghiou: Department of Chemistry, Memorial University of Newfoundland, St. John’s, Newfoundland and Labrador A1B3X7, Canada
Kanchugarakoppal S. Rangappa: Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka 570 006, India
Maralinganadoddi P. Sadashiva: Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka 570 006, India

DOI: https://doi.org/10.3762/bjoc.16.18
Journal volume & issue: Vol. 16, no. 1
pp. 159 – 167

Abstract

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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.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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