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Polycyclic [2+3]-Cycloadducts from the Thermal Decomposition of Bis(2,5-dihydro-1,3,4-thiadiazoles) in the Presence of N-Methylmaleimide


Mloston, Grzegorz; Celeda, Malgorzata; Linden, Anthony; Heimgartner, Heinz (2004). Polycyclic [2+3]-Cycloadducts from the Thermal Decomposition of Bis(2,5-dihydro-1,3,4-thiadiazoles) in the Presence of N-Methylmaleimide. Polish Journal of Chemistry, 78(11-12):2089-2099.

Abstract

Thermal decomposition of a mixture of the two stereoisomeric bis(2,5-dihydro-1,3,4-thiadiazoles) cis- and trans-2, which was prepared by treatment of 2,2,4,4-tetramethylcyclobutane-1,3-dithione with excess of diazomethane in the presence of two equivalents of N-methylmaleimide, led to a mixture of three 1:2 cycloadducts of type 4. The structures of these thiocarbonyl methanide-adducts have been established by X-ray crystallography. In the presence of only one equivalent of N-methylmaleimide, a complex mixture of the three 1:2 adducts of type 4, the known dispirocyclic bis-thiiranes cis- and trans-3, and a 1:1 adduct 6, containing one thiirane ring and one fragment resulting from a [2+3]-cycloaddition of a thiocarbonyl methanide, was formed. The structure of the latter has again been proven by X-ray crystallography.

Abstract

Thermal decomposition of a mixture of the two stereoisomeric bis(2,5-dihydro-1,3,4-thiadiazoles) cis- and trans-2, which was prepared by treatment of 2,2,4,4-tetramethylcyclobutane-1,3-dithione with excess of diazomethane in the presence of two equivalents of N-methylmaleimide, led to a mixture of three 1:2 cycloadducts of type 4. The structures of these thiocarbonyl methanide-adducts have been established by X-ray crystallography. In the presence of only one equivalent of N-methylmaleimide, a complex mixture of the three 1:2 adducts of type 4, the known dispirocyclic bis-thiiranes cis- and trans-3, and a 1:1 adduct 6, containing one thiirane ring and one fragment resulting from a [2+3]-cycloaddition of a thiocarbonyl methanide, was formed. The structure of the latter has again been proven 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:2004
Deposited On:19 Aug 2013 06:24
Last Modified:05 Apr 2016 16:54
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish State Committee for Scientific Research (Grant No. 4 T09A 046 25), F. Hoffmann-La Roche AG, Basel
Related URLs:http://www.ichf.edu.pl/pjch/pj-2004.htm

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