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Reactions of Thioketones with Methyl Azidoacetate


Mloston, Grzegorz; Romanski, Jaroslaw; Linden, Anthony; Heimgartner, Heinz (1996). Reactions of Thioketones with Methyl Azidoacetate. Polish Journal of Chemistry, 70(7):880-890.

Abstract

The reaction of methyl azidoacetate with several thiocarbonyl compounds at 80°C leads to imine derivatives of methyl glycinate in yields of about 60%. With 2,2,4,4-tetramethyl-3-thioxocyclobutanone, only 19% of the corresponding glycinate 19 is obtained. The main products in this reaction are the symmetrical dispiro-1,2,4-trithiolane 20 and the dispiro-1,4,2-dithiazolidine 21 (Scheme 6). The structure of the latter was established by X-ray crystallography. A reaction mechanism involving an intermediate thiocarbonyl-S-sulfide and a thiocarbonyl-S-imide is proposed in Scheme 2.

Abstract

The reaction of methyl azidoacetate with several thiocarbonyl compounds at 80°C leads to imine derivatives of methyl glycinate in yields of about 60%. With 2,2,4,4-tetramethyl-3-thioxocyclobutanone, only 19% of the corresponding glycinate 19 is obtained. The main products in this reaction are the symmetrical dispiro-1,2,4-trithiolane 20 and the dispiro-1,4,2-dithiazolidine 21 (Scheme 6). The structure of the latter was established by X-ray crystallography. A reaction mechanism involving an intermediate thiocarbonyl-S-sulfide and a thiocarbonyl-S-imide is proposed in Scheme 2.

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11 citations in Web of Science®
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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 08:12
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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