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Reaction of carbon disulfide with azide ion

Lieber, Eugene and Oftedahl, Edwin and Rao, CNR (1963) Reaction of carbon disulfide with azide ion. In: Journal of Organic Chemistry, 28 (1). pp. 194-199.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo01036a046


Carbon disulfide reacts with azide ion to form the 1,2,3,4-thiatriazolinethionate ion and not the acyclic azido dithiocarbonate ion as previously reported. A series of salts of thiatriazoline have been prepared and none shows evidence for the presence of the azido group. Esters of thiatriazolinethione prepared by the reaction of the sodium salt with alkyl or acyl halides have been found to be either 5-(substituted) mercapto-1,2,3,4-thiatriazoles or 4-substituted 1,2,3,4-thiatriazoline-5-thiones. These structures have been assigned on the basis of degradative and spectroscopic evidence. The chemistry of the so-called azidodithiocarbonates has been reinterpreted in terms of the thiatriazole structure.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited: 24 May 2010 10:38
Last Modified: 22 Nov 2018 15:04
URI: http://eprints.iisc.ac.in/id/eprint/28104

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