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Sulfur centered 1,3-Dipoles. An efficient trapping of Adamantanethione-S-sulfide generated in the reaction of Adamantanethione with organic azides


Mloston, Grzegorz; Romanski, Jaroslaw; Heimgartner, Heinz (1996). Sulfur centered 1,3-Dipoles. An efficient trapping of Adamantanethione-S-sulfide generated in the reaction of Adamantanethione with organic azides. Polish Journal of Chemistry, 70(4):437-445.

Abstract

The reaction of adamantanethione (1) and an organic azide at 80°C ("two-component reaction") yields the symmetrical 1,2,4-trithiolane 9 and the corresponding adamantylidene imine 10 in nearly equal amounts. Under the same conditions, the "three-component reaction" with 1, phenyl azide and an aromatic thioketone gives the unsymmetrical 1,2,4-trithiolane 12 as the major product, and 9 and imine 13 as by-products. A 1,3-dipolar cycloaddition of an intermediate thiocarbonyl-S-sulfide and a thioketone is proposed as the mechanism for the formation of the trithiolanes. The structure of trithiolane 12a has been established by X-ray crystallography.

Abstract

The reaction of adamantanethione (1) and an organic azide at 80°C ("two-component reaction") yields the symmetrical 1,2,4-trithiolane 9 and the corresponding adamantylidene imine 10 in nearly equal amounts. Under the same conditions, the "three-component reaction" with 1, phenyl azide and an aromatic thioketone gives the unsymmetrical 1,2,4-trithiolane 12 as the major product, and 9 and imine 13 as by-products. A 1,3-dipolar cycloaddition of an intermediate thiocarbonyl-S-sulfide and a thioketone is proposed as the mechanism for the formation of the trithiolanes. The structure of trithiolane 12a has been established by X-ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1996
Deposited On:25 Nov 2013 08:09
Last Modified:07 Dec 2017 23:57
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish State Committee for Scientific Research (Grant No. 3 TO9A 157 10), Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Related URLs:http://www.ichf.edu.pl/pjch/

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