The hetero-Diels-Alder addition of sulfur dioxide to (E)- and (Z)-4-(fluoromethylidene)-3-methylene-2,3-dihydro-naphthalene follows the endo Alder rule. The first example of a crystalline sultine has been obtained. In agreement with high level quantum calculations, (1SR,3SR)-1-fluoro-1,4,5,6-tetrahydronaphtho[2,1-d][1,2]oxathiine 3-oxide adopts a sofa conformation in its ground state.
Title
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
Published in
Chemical Communications
Issue
13
Pages
1214-1215
Date
2001
ISSN
1359-7345
Note
Univ Oviedo, Dept Quim Fis & Analit, Lab Quim Computac, E-33071 Oviedo, Spain. Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland.
Record creation date
2005-11-09