Sulfoxide



  A sulfoxide is a sulfides. (The use of the alternative name sulphoxide is discouraged by IUPAC.) An example of a sulfoxide occurring in nature is alliin.

Nature of the bond

Sulfoxides are generally represented with the structural formula R-S(=O)-R', where R and R' are organic groups. The bond between the oxygen atoms differs from the conventional double bond between carbon and oxygen in, say, ketones. The S-O interaction has a electrostatic aspect, resulting in significant dipolar character, with negative charge centered on oxygen. The bonding is similar to that in tertiary phosphine oxides, R3P=O.

A chiral center, for example, methylphenylsulfoxide.

The energy required to invert this transition metal and a chiral ligand.

Reactions

Sulfides are the usual starting materials to sulfoxides by organic oxidation. For example, dimethyl sulfone wherein sulfur has the oxidation state +2.

Sulfoxides, such as sodium hydride.[2]

References

  1. ^ Oxidation of sulfides to chiral sulfoxides using Schiff base-vanadium (IV) complexes Ángeles Gama, Lucía Z. Flores-López, Gerardo Aguirre, Miguel Parra-Hake, Lars H. Hellberg, and Ratnasamy Somanathan Arkivoc MX-789E 2003 Online article
  2. ^ Iwai, I.; Ide, J. "2,3-Diphenyl-1,3-Butadiene" Organic Syntheses, Collected Volume 6, p.531 (1988). http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV6P0531.pdf.
 
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