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  4. The hetero-Diels-Alder addition of sulfur dioxide: The pseudo-chair conformation of a 4,5-dialkylsultine
 
research article

The hetero-Diels-Alder addition of sulfur dioxide: The pseudo-chair conformation of a 4,5-dialkylsultine

Markovic, D.  
•
Roversi, E.
•
Seoppelliti, R.
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2003
Chemistry-a European Journal

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 -100degreesC 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.

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Type
research article
DOI
10.1002/chem.200304932
Web of Science ID

WOS:000186151700008

Author(s)
Markovic, D.  
Roversi, E.
Seoppelliti, R.
Vogel, P.  
Meana, R.
Sordo, J. A.
Date Issued

2003

Published in
Chemistry-a European Journal
Volume

9

Issue

20

Start page

4911

End page

4915

Subjects

ab initio calculations

•

conformation analysis

•

cycloadditions

•

heterocycles

•

sulfur

•

Cheletropic additions

•

quantum calculations

•

competition

•

1

•

3-dienes

•

2

•

5-dihydrothiophene-1

•

1-dioxides

•

stereoselectivity

•

regioselectivity

•

buta-1

•

3-dienes

•

sulfolenes

•

sultines

•

2

•

3-dienes

Note

BCH, Swiss Inst Technol, Inst Mol & Biol Chem, CH-1015 Lausanne, Switzerland. Univ Oviedo, Dept Quim Fis & Analit, Lab Quim Computac, E-33071 Oviedo, Principado Astu, Spain.

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219813
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