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27.1.3 Product Subclass 3: Sulfonium Ylides

DOI: 10.1055/sos-SD-027-00002

Aggarwal, V.; Richardson, J.Science of Synthesis, (20042759.

The first report of an isolable sulfonium ylide (dimethylsulfonium 9H-fluoren-9-ylide) was made by Ingold and Jessop in 1930.[‌179‌] Since that time, sulfonium ylides have become widely employed in synthesis. There exists a broad range of ylide stabilities, from stable crystalline species to those that are impossible to isolate, existing only as transient intermediates. Sulfonium ylides are less stable than the corresponding sulfoxonium ylides, due primarily to the extra electron density on sulfur, in the form of a lone pair of electrons, which slightly destabilizes the adjacent carbanion.

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