text: Phosphonium ylides are used in the Wittig reaction, a method used to convert ketones and especially aldehydes to alkenes. The positive charge in these Wittig reagents is carried by a phosphorus atom with three phenyl substituents and a bond to a carbanion.  Ylides can be stabilised or non-stabilised. A phosphonium ylide can be prepared rather straightforwardly. Typically, triphenylphosphine is allowed to react with an alkyl halide in a mechanism analogous to that of an S2 reaction. This quaternization forms an alkyltriphenylphosphonium salt, which can be isolated or treated in situ with a strong base (in this case, butyllithium) to form the ylide.
  Due to the S2 mechanism, a less sterically hindered alkyl halide reacts more favorably with triphenylphosphine than an alkyl halide with significant steric hindrance (such as tert-butyl bromide). Because of this, there will typically be one synthetic route in a synthesis involving such compounds that is more favorable than another.
  Phosphorus ylides are important reagents in organic chemistry, especially in the synthesis of naturally occurring products with
  biological and pharmacological activities. Much of the interest in the coordination properties of a-keto stabilized phosphorus
  ylides stems from their coordination versatility due to the presence of different functional groups in their molecular structure.