Publication

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

Pierre Vogel
2003
Journal Articles

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 -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.

Official source

https://infoscience.epfl.ch/entities/publication/1fe212a0-17d0-4617-8a75-08229ca38d1c

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Pierre Vogel
2003
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/1fe212a0-17d0-4617-8a75-08229ca38d1c

About this result

Related concepts (26)

1,3-Dipolar cycloaddition

The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic application were established in the 1960s, primarily through the work of Rolf Huisgen. Hence, the reaction is sometimes referred to as the Huisgen cycloaddition (this term is often used to specifically describe the 1,3-dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-triazole).

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

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