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Regioselektive 1,3-dipolare Cycloadditionen von Thiocarbonyl-yliden mit 1,3-Thiazol-5(4H)-thionen


Mloston, Grzegorz; Linden, Anthony; Heimgartner, Heinz (1991). Regioselektive 1,3-dipolare Cycloadditionen von Thiocarbonyl-yliden mit 1,3-Thiazol-5(4H)-thionen. Helvetica Chimica Acta, 74(7):1386-1398.

Abstract

The thiocarbonyl ylides 13 and 1,3-thiazol-5(4H)-thiones 1 undergo a smooth reaction to yield spirocyclic 1,3-dithioIanes 14-16 (Schemes 4-6) . The 1,3-dipolar cycloadditions occur in a regioselective manner, but the orientation of the thiobenzophenone-S-methylide (13b) differs from that of the cycloalkane thione-S-methylides 13a and 13c. Whereas the 1,3-cycloadduct with 13b is formed in accordance with frontier-orbital considerations, the inverse orientation in the reactions with 13a and 13c most likely is the result of steric hindrance in the transition state. The thiocarbonyl ylides have been prepared in situ from the corresponding 2,5-dihydro-1,3,4-thiadiazoles 12. The more stable aliphatic precursors 12a and 12c undergo decomposition at 50", the unstable 12b at -30".

Abstract

The thiocarbonyl ylides 13 and 1,3-thiazol-5(4H)-thiones 1 undergo a smooth reaction to yield spirocyclic 1,3-dithioIanes 14-16 (Schemes 4-6) . The 1,3-dipolar cycloadditions occur in a regioselective manner, but the orientation of the thiobenzophenone-S-methylide (13b) differs from that of the cycloalkane thione-S-methylides 13a and 13c. Whereas the 1,3-cycloadduct with 13b is formed in accordance with frontier-orbital considerations, the inverse orientation in the reactions with 13a and 13c most likely is the result of steric hindrance in the transition state. The thiocarbonyl ylides have been prepared in situ from the corresponding 2,5-dihydro-1,3,4-thiadiazoles 12. The more stable aliphatic precursors 12a and 12c undergo decomposition at 50", the unstable 12b at -30".

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Additional indexing

Other titles:Regioselective 1,3-Dipolar Cycloadditions of Thiocarbonyl Ylides with 1,3-Thiazole-5(4H)-thiones
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1991
Deposited On:13 Mar 2014 08:16
Last Modified:05 Apr 2016 17:26
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Polnische Akademie der Wissenschaften , Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19910740703

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