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The Finkelstein reaction, named after the German chemist Hans Finkelstein, [1] is a type of S N 2 reaction (substitution nucleophilic bimolecular reaction) that involves the exchange of one halogen atom for another.
This kind of reaction is called Finkelstein reaction. [2] However, it is also possible, for example, to produce phosphorus fluoride compounds by transhalogenating chlorine, bromine or iodine bound to phosphorus with a metal fluoride. [3]
Hans Finkelstein (17 May 1885, Leipzig, Germany - December 1938) was a German chemist. He is particularly known for the Finkelstein reaction developed by and named after him. [ 1 ] [ 2 ]
Conant studied the effect of haloalkane structure on the rate of substitution with inorganic iodide salts [19] which, together with earlier work, [20] led to what is now known as either the Conant-Finkelstein reaction or more commonly simply the Finkelstein reaction. [21]
However, if an unreactive alkylating agent is used (e.g. an alkyl chloride) then the rate of reaction can be greatly improved by the addition of a catalytic quantity of a soluble iodide salt (which undergoes halide exchange with the chloride to yield a much more reactive iodide, a variant of the Finkelstein reaction).
The iodide anion is a good nucleophile and will displace chloride, tosylate, bromide and other leaving groups, as in the Finkelstein reaction. Alcohols can be converted to the corresponding iodides using phosphorus triiodide. Illustrative is the conversion of methanol to iodomethane: [15] PI 3 + 3 CH 3 OH → 3 CH 3 I + "H 3 PO 3 "
Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction. Reaction with other pseudohalides such as azide, cyanide, and thiocyanate are possible as well. In the presence of a strong base, alkyl chlorides undergo dehydrohalogenation to give alkenes or alkynes.
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