Issue 13, 2001
From the journal:

Chemical Communications

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-oxidesElectronic supplementary information (ESI) available: synthetic procedures, data for (E)-3, (Z)-3, 4 and 5. Crystal and molecular structures of 5, tables of calculated data and representations of calculated minima and transition structures. See http://www.rsc.org/suppdata/cc/b1/b103096p/

Elena Roversi,a   Rosario Scopelliti,a   Euro Solari,a   Raphaël Estoppey,a   Pierre Vogel,*a   Pedro Braña,b   Bibiana Menéndezb  and  José Ángel Sordo*b  

* Corresponding authors

a Section de chimie de l’Université de Lausanne, BCH, Lausanne-Dorigny, Switzerland.
E-mail: pierre.vogel@ico.unil.ch;
Fax: (+41) 21 692 3955

b Laboratorio de Química Computacional, Departamento de Química Física y Analítica, Universidad de Oviedo, Oviedo, Spain

Abstract

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.

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Supplementary files

Article information

DOI
https://doi.org/10.1039/B103096P
Article type
Communication
Submitted
05 Apr 2001
Accepted
18 May 2001
First published
14 Jun 2001

Chem. Commun., 2001, 1214-1215

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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

E. Roversi, R. Scopelliti, E. Solari, R. Estoppey, P. Vogel, P. Braña, B. Menéndez and J. Sordo, Chem. Commun., 2001, 1214 DOI: 10.1039/B103096P

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