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2-Alkylidene-4-oxothiazolidine S-oxides - synthesis and stereochemistry

  • A series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization to the mixture enriched in the more stable syn-isomer, during the work-up process. The higher stability of syn-isomers is ascribed to the stronger hyperconjugative sigma(C-H)->sigma*(S-O) interaction versus the weaker sigma(C-C)->sigma*(S-O) delocalization in their anti-counterparts and to the existence of intramolecular 1,5-CH center dot center dot center dot C hydrogen bonds.

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Metadaten
Author:Zdravko Dzambaski, Rade Markovic, Erich Kleinpeter, Marija Baranac-Stojanovic
DOI:https://doi.org/10.1016/j.tet.2013.05.087
ISSN:0040-4020 (print)
Parent Title (English):Tetrahedron
Publisher:Elsevier
Place of publication:Oxford
Document Type:Article
Language:English
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
Tag:2-Alkylidene-4-oxothiazolidine; CH center dot center dot center dot O hydrogen bonds; Density functional calculations; Diastereoselectivity; Sulfoxide
Volume:69
Issue:31
Pagenumber:12
First Page:6436
Last Page:6447
Funder:Ministry of Education, Science and Technological Development of the Republic of Serbia [172020]; Deutscher Akademischer Austauschdienst (DAAD) [504 252 70]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert