Publication

Four component synthesis of (Z)-4-alkoxy-1,3-dimethylalk-2-enyl methyl sulfones: on the intermediacy of sultines (3,6-dihydro-1,2-oxathiin-2-oxides) arising from suprafacial hetero-Diels-Alder additions of sulfur dioxide

Pierre Vogel
2001
Journal Articles

Abstract

The reactions of (E,E)-1-benzyloxy-2-methylpenta-1,3-diene (9) with 3,3-dimethyl-2-(trimethylsilyloxy)butene and (Z)-3-(trimethylsilyloxy)pent-2-ene in SO2 and a Lewis acid give silyl sulfinates that are quenched with Met to generate the corresponding (Z)-4-benzyloxy-1,3-dimethylalk-2-enyl methyl sulfones with unlike relative configuration at C-l and C-4 (by X-ray diffraction studies), in support of processes involving the intermediacy of a sultine arising from the suprafacial hetero-Diels-Alder addition of SO2 to diene 9. (C) 2001 Elsevier Science Led. All rights reserved.

Official source

https://infoscience.epfl.ch/entities/publication/3e539664-1292-415d-a8d3-962e15da7aaa

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Pierre Vogel
2001
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3e539664-1292-415d-a8d3-962e15da7aaa

About this result

Related concepts (18)

Sulfur dioxide

Sulfur dioxide (IUPAC-recommended spelling) or sulphur dioxide (traditional Commonwealth English) is the chemical compound with the formula SO2. It is a toxic gas responsible for the odor of burnt matches. It is released naturally by volcanic activity and is produced as a by-product of copper extraction and the burning of sulfur-bearing fossil fuels. SO2 is a bent molecule with C2v symmetry point group. A valence bond theory approach considering just s and p orbitals would describe the bonding in terms of resonance between two resonance structures.

Sulfur

Sulfur (also spelled sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula S8. Elemental sulfur is a bright yellow, crystalline solid at room temperature. Sulfur is the tenth most abundant element by mass in the universe and the fifth most on Earth. Though sometimes found in pure, native form, sulfur on Earth usually occurs as sulfide and sulfate minerals.

Sulfuric acid

Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, and hydrogen, with the molecular formula . It is a colorless, odorless, and viscous liquid that is miscible with water. Pure sulfuric acid does not occur naturally due to its strong affinity to water vapor; it is hygroscopic and readily absorbs water vapor from the air.