The Hetero-Diels-Alder Addition of Sulfur Dioxide: The Pseudo-Chair Conformation of a 4,5-Dialkylsultine

Dean Markovic, Elena Roversi, Rosario Scoppelliti, Pierre Vogel, Ruben Meana Paneda, José A. Sordo

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Even unsubstituted butadiene adds to sulfur dioxide in the hetero-Diels-Alder mode more rapidly than in the chelotropic mode. The sultine can be observed in equilibrium with the diene and the sulfur dioxide only at low temperature and in the presence of CF3COOH. Crystals of 4,5-dialkyl-sultine resulting from the SO2 addition to 1,2-dimethylidenecyclohexane have been obtained at -100°C and analyzed by X-ray diffraction. Quantum chemical calculations have shown that hyperconjugative interactions within the sulfinyl moiety are responsible for the anomeric effects observed in sultines that prefer pseudo-chair conformations with pseudo-axial S=O bonds.

Original languageEnglish (US)
Pages (from-to)4911-4915
Number of pages5
JournalChemistry - A European Journal
Volume9
Issue number20
DOIs
StatePublished - Oct 17 2003

Keywords

  • Ab initio calculations
  • Conformation analysis
  • Cycloadditions
  • Heterocycles
  • Sulfur

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    Markovic, D., Roversi, E., Scoppelliti, R., Vogel, P., Meana Paneda, R., & Sordo, J. A. (2003). The Hetero-Diels-Alder Addition of Sulfur Dioxide: The Pseudo-Chair Conformation of a 4,5-Dialkylsultine. Chemistry - A European Journal, 9(20), 4911-4915. https://doi.org/10.1002/chem.200304932