Science of Synthesis

Aggarwal, V.; Richardson, J., Science of Synthesis, (2004) 27, 63.

Due to the success of other methods for the generation of sulfonium ylides, hydrogen-substitution reactions are not as common as they are for sulfoxonium ylides. Most commonly, acylations (or related reactions) of stabilized ylides are performed. Hydrogen-substitution of nonstabilized ylides has not been performed as easier routes to prepare such compounds already exist. However, this method for ylide generation can be applied in two structural situations: (1) if the ylide formed is more stable than the starting ylide, then regioselective deprotonation will occur using the starting ylide or excess base; and (2) ylide destabilizing groups, such as alkyl substituents, can be added when the resulting sulfonium salt has no other α-hydrogens and thus any excess base will, if of sufficient strength, form the substituted ylide.

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