The Kirsanov reaction is a method for the synthesis of certain
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 ...
s. In this reaction a tertiary phosphine is combined with a halogen and then an amine to give the iminophosphines, which are useful
ligands and useful
reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
s.
A typical reaction involves
triphenylphosphine with
bromine to give bromotriphenyl
phosphonium
In polyatomic cations with the chemical formula (where R is a hydrogen or an alkyl, aryl, or halide group). These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.
Types of phosphonium ...
bromide:
:Ph
3P + Br
2 → Ph
3PBr
+Br
−
This salt is treated in situ with alkylamines to give the iminophosphorane:
:Ph
3PBr
+Br
− + 3 RNH
2 → Ph
3PNR + 2 RNH
3+Br
−
The method is used when the conventional
Staudinger reaction
The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered by and named after Hermann Staudinger. The reaction follows this stoichiometry:
:R3P + ...
is not applicable, i.e. when the organic azide is not available to generate the iminophosphorane. Thus, it is used to make iminophosphoranes from alkyl amines.
[{{cite journal, last1=Buchard, first1=Antoine, last2=Heuclin, first2=Hadrien, last3=Auffrant, first3=Audrey, last4=Le Goff, first4=Xavier F., last5=Le Floch, first5=Pascal, title=Coordination of tetradentate X2N2 (X = P, S, O) ligands to iron(ii) metal center and catalytic application in the transfer hydrogenation of ketones, journal=Dalton Transactions, date=2009, issue=9, pages=1659–67, doi=10.1039/b816439h, pmid=19421611]
References
Name reactions