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Abstract
In our recent project we focused on reactivity of2,2-dimethyl-4,6-dioxane-1,3-dione carbamoilo- and thiocarbamoylo- derivatives as a ketenesource. Meldrum`s acid derivatives after thermal decomposition gives substituted keteneswith stoichiometric yield, that can be trapped with various spectrum of nucleophiles likealcohols, thiols, amine, imines etc. In case of5-[3-(dimethylamino)-sulfanyl-propyliden]-2,2-dimethyl-1,3-dioxane-4,6-dione after heatingin the presence of various amines we isolated main unexpected product2,2-dimethyl-5-[1,3-thiazolidin-2-ylidene)-1,3-dioxane-4,6-dione. The compound that weobtained, indicates that in this reaction instead of thermal decomposition to ketene, occurssubstitution of dimethylamine by sulfanyl group, resulting in closure of 1,3-thiazolidin ring.We are dealing here with unusual case in which secondary amine in basic conditions works asa leaving group. This exclude compound as a ketene source, however phenomenon is ancurious case of irregular behavior of secondary amine group.
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- Category:
- Monographic publication
- Type:
- rozdział, artykuł w książce - dziele zbiorowym /podręczniku w języku o zasięgu międzynarodowym
- Title of issue:
- ''Advances in Chemical and Mechanical Engineering''. - Vol. II/II strony 159 - 160
- Language:
- English
- Publication year:
- 2012
- Bibliographic description:
- Punda P.: Unusual behavior of secondary amine group as a leaving group// ''Advances in Chemical and Mechanical Engineering''. - Vol. II/II/ ed. eds. C. Fijało, P. Fijało. - Gdansk University of Technology. Gdańsk: GUT, 2012, s.159-160
- Verified by:
- Gdańsk University of Technology
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