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Thio- and Dithioesters as Dipolarophiles in reactions with Thiocarbonyl Ylides


Urbaniak, Katarzyna; Mloston, Grzegorz; Gulea, Mihaela; Masson, Serge; Linden, Anthony; Heimgartner, Heinz (2005). Thio- and Dithioesters as Dipolarophiles in reactions with Thiocarbonyl Ylides. European Journal of Organic Chemistry, 2005(8):1604-1612.

Abstract

The thiocarbonyl S-methylides 3a–c, generated in situ by thermal decomposition of the corresponding 2,5-dihydro-1,3,4-thiadiazoles, undergo [3+2] cycloadditions with diphenyltrithiocarbonate (5a) to give 1,3-dithiolanes. The regioselectivity of the reaction of the cycloaliphatic dipoles 3b and 3c is reversed in comparison with that of the aromatic 3a. A mixture of both regioisomeric cycloadducts is formedin the reaction between 3b and methyl dithiobenzoate (6a), whereas only one regioisomer is obtained with thiophthalide (7). Dialkyl phosphonodithioformates 8 are shown to be efficient C=S dipolarophiles in reactions with thiocarbonyl Smethylides 3a–3d, affording 1,3-dithiolane-4-phosphonates.

Abstract

The thiocarbonyl S-methylides 3a–c, generated in situ by thermal decomposition of the corresponding 2,5-dihydro-1,3,4-thiadiazoles, undergo [3+2] cycloadditions with diphenyltrithiocarbonate (5a) to give 1,3-dithiolanes. The regioselectivity of the reaction of the cycloaliphatic dipoles 3b and 3c is reversed in comparison with that of the aromatic 3a. A mixture of both regioisomeric cycloadducts is formedin the reaction between 3b and methyl dithiobenzoate (6a), whereas only one regioisomer is obtained with thiophthalide (7). Dialkyl phosphonodithioformates 8 are shown to be efficient C=S dipolarophiles in reactions with thiocarbonyl Smethylides 3a–3d, affording 1,3-dithiolane-4-phosphonates.

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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:2005
Deposited On:27 Mar 2013 08:20
Last Modified:07 Dec 2017 16:51
Publisher:Wiley-Blackwell
ISSN:1099-0690
Funders:Polish State Committee for Scientific Research, French CNRS, European Union (FEDER funding), Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/ejoc.200400737

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