McCormack reaction
Encyclopedia
The McCormack reaction is a method for the synthesis of organophosphorus compounds. In this reaction a 1,3-diene
and a source of R2P+ are combined to give phospholenium cation. The reaction is named after W. B. McCormack, a research chemist at duPont.
An illustrative reaction involves phenyldichlorophosphine and isoprene
:
The reaction proceeds via an pericyclic [1+4]-process. The resulting derivatives can be hydrolyzed to give the phosphine oxide
. Dehydrohalogenation
gives the phosphole
.
Diene
In organic chemistry a diene or diolefin is a hydrocarbon that contains two carbon double bonds.Conjugated dienes are functional groups, with a general formula of CnH2n-2. Dienes and alkynes are functional isomers...
and a source of R2P+ are combined to give phospholenium cation. The reaction is named after W. B. McCormack, a research chemist at duPont.
An illustrative reaction involves phenyldichlorophosphine and isoprene
Isoprene
Isoprene , or 2-methyl-1,3-butadiene, is a common organic compound with the formula CH2=CCH=CH2. Under standard conditions it is a colorless liquid...
:
The reaction proceeds via an pericyclic [1+4]-process. The resulting derivatives can be hydrolyzed to give the phosphine oxide
Phosphine oxide
Phosphine oxides are either inorganic phosphorus compounds such as phosphoryl trichloride or organophosphorus compounds with the formula OPR3, where R = alkyl or aryl...
. Dehydrohalogenation
Dehydrohalogenation
Dehydrohalogenation is an organic reaction from which an alkene is obtained from an alkyl halide . It is also called a β-Elimination reaction and is a type of elimination reaction....
gives the phosphole
Phosphole
Phosphole is the organic compound with the chemical formula C4H4PH; it is the phosphorus analog of pyrrole. The term phosphole also refers to substituted derivatives of the parent heterocycle...
.