(Chloromethylene)triphenylphosphorane is the

organophosphorus compound Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...

with he formula Ph₃P=CHCl (Ph =

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

). It is a white solid but is usually generated and used in situ as a reagent in

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

. It is structurally and chemically related to

methylenetriphenylphosphorane Methylenetriphenylphosphorane is an organophosphorus compound with the formula Ph3PCH2. It is the parent member of the phosphorus ylides, popularly known as Wittig reagents. It is a highly polar, highly basic species. Preparation and use Methylene ...

. The reagent is prepared from the chloromethylphosphonium salt h₃PCH₂Cll by treatment with strong base. The phosphonium compound is generated by treatment of

triphenylphosphine Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists a ...

with

chloroiodomethane Chloroiodomethane is the halomethane with the formula is . It is a colorless liquid of use in organic synthesis. Together with other iodomethanes, chloroiodomethane is produced by some microorganisms. Applications Chloroiodomethane is used in cyc ...

. (Chloromethylene)triphenylphosphorane converts

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

s to vinyl chlorides: :RCHO + Ph₃P=CHCl → RCH=CHCl + Ph₃PO These vinyl chlorides undergo

dehydrochlorination In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl hali ...

to give

alkyne \ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...

s: :RCH=CHCl + NaN(SiMe₃)₂ → RC≡CH + NaCl + HN(SiMe₃)₂

Related compounds

*(Iodomethylene)triphenylphosphorane *(Dichloromethylene)triphenylphosphorane

References

{{DEFAULTSORT:Chloromethylene)triphenylphosphorane Organophosphorus compounds