Reaction of carbon disulfide with azide ion

Lieber, Eugene ; Oftedahl, Edwin ; Rao, C. N. R. (1963) Reaction of carbon disulfide with azide ion Journal of Organic Chemistry, 28 (1). pp. 194-199. ISSN 0022-3263

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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:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:43559
Deposited On:11 Jun 2011 14:56
Last Modified:11 Jun 2011 14:56

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