@article{DzambaskiMarkovicKleinpeteretal.2013,
  author    = {Dzambaski, Zdravko and Markovic, Rade and Kleinpeter, Erich and Baranac-Stojanovic, Marija},
  title     = {2-Alkylidene-4-oxothiazolidine S-oxides - synthesis and stereochemistry},
  series = {Tetrahedron},
  volume    = {69},
  journal   = {Tetrahedron},
  number    = {31},
  publisher = {Elsevier},
  address   = {Oxford},
  issn      = {0040-4020},
  doi       = {10.1016/j.tet.2013.05.087},
  pages     = {6436 -- 6447},
  year      = {2013},
  abstract  = {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.},
  language  = {en}
}