(Chloromethylene)triphenylphosphorane is the
organophosphorus compound with the formula Ph
3P=CHCl (Ph =
phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...
). It is a white solid but is usually generated and used in situ as a reagent in
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
. It is structurally and chemically related to
methylenetriphenylphosphorane.
The reagent is prepared from the chloromethylphosphonium salt
h3PCH2Cll by treatment with strong base. The phosphonium compound is generated by treatment of
triphenylphosphine with
chloroiodomethane.
(Chloromethylene)triphenylphosphorane converts
aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
s to
vinyl chlorides:
:RCHO + Ph
3P=CHCl → RCH=CHCl + Ph
3PO
These vinyl chlorides undergo
dehydrochlorination 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(SiMe
3)
2 → RC≡CH + NaCl + HN(SiMe
3)
2
Related compounds
*(Iodomethylene)triphenylphosphorane
*(Dichloromethylene)triphenylphosphorane
References
{{DEFAULTSORT:Chloromethylene)triphenylphosphorane
Organophosphorus compounds