The hetero-Diels-Alder addition of sulfur dioxide: structure of the first crystalline sultine. Quantum calculations on the conformations of 6-fluoro-3,6-dihydro-1,2-oxathiine 2-oxides

Authors
Roversi, E Scopelliti, R Solari, E Estoppey, R Vogel, P Brana, P Menendez, B Sordo, JA
Citation
E. Roversi et al., The hetero-Diels-Alder addition of sulfur dioxide: structure of the first crystalline sultine. Quantum calculations on the conformations of 6-fluoro-3,6-dihydro-1,2-oxathiine 2-oxides, CHEM COMMUN, (13), 2001, pp. 1214-1215
Citations number
15
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
13
Year of publication
2001
Pages
1214 - 1215
Database
ISI
SICI code
1359-7345(2001):13<1214:THAOSD>2.0.ZU;2-K
Abstract
The hetero-Diels-Alder addition of sulfur dioxide to (E)- and (Z)-4-(fluoro methylidene)-3-methylene-2,3-dihydro-naphthalene follows the endo Alder rul e. The first example of a crystalline sultine has been obtained. In agreeme nt with high level quantum calculations, (1SR,3SR)-1-fluoro-1,4,5,6-tetrahy dronaphtho[2,1-d][1,2]oxathiine 3-oxide adopts a sofa conformation in its g round state.