10.2.2 Rearrangement of Sulfur Ylides

Sulfur ylides rearrange as shown in Scheme 4. In case of allylic sulfur ylide, [3,2]-sigmatropic rearrangement is observed.

Scheme 4

Aza- and oxa-sulfonium salts give ylides that can rearrange to give useful aromatic compounds (Scheme 5).

Scheme 5

10.2.2 Reactions of the Dimsyl Anion

Dimsyl anion is very reactive nucleophile and can be used for various synthetic applications. The sulfur substituent can be easily removed by reduction or thermally (Scheme 6).

Scheme 6