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Generation and [2+3]cycloadditions of a sulfonylated thiocarbonyl S-methanide


Urbaniak, Katarzyna; Sobieraj, Magdalena; Mlostoń, Grzegorz; Linden, Anthony; Heimgartner, Heinz (2005). Generation and [2+3]cycloadditions of a sulfonylated thiocarbonyl S-methanide. Heterocycles, 65(6):1373-1383.

Abstract

The sulfonylated thiocarbonyl S-methanide (2a) was generated in situ by addition of diazomethane to the C-sulfonylated dithioformate (1a) and subsequent thermal elimination of nitrogen. This 1,3-dipole was intercepted by C,C- and C,S-dipolarophiles. Whereas in the first case the cycloadducts (10) and (11) could be isolated as stable products, the cycloadducts of type (8), which are the proposed products of the reaction with thioketones, underwent a spontaneous rearrangement to give open-chain ketene dithioacetals (5) and (6).

Abstract

The sulfonylated thiocarbonyl S-methanide (2a) was generated in situ by addition of diazomethane to the C-sulfonylated dithioformate (1a) and subsequent thermal elimination of nitrogen. This 1,3-dipole was intercepted by C,C- and C,S-dipolarophiles. Whereas in the first case the cycloadducts (10) and (11) could be isolated as stable products, the cycloadducts of type (8), which are the proposed products of the reaction with thioketones, underwent a spontaneous rearrangement to give open-chain ketene dithioacetals (5) and (6).

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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
Scopus Subject Areas:Physical Sciences > Analytical Chemistry
Life Sciences > Pharmacology
Physical Sciences > Organic Chemistry
Language:English
Date:2005
Deposited On:23 Jul 2012 12:32
Last Modified:30 Jul 2020 05:27
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Polish Committee for Scientific Research (Grant No. 4 T09A 046 25), F. Hoffmann-La Roche AG, Basel
OA Status:Green
Publisher DOI:https://doi.org/10.3987/COM-05-10373

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