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The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol . This reaction was developed by Alexander Williamson in 1850. [ 2 ] Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an S N 2 reaction .
Alexander Williamson. Williamson is credited for his research on the formation of unsymmetrical ethers by the interaction of an alkoxide with a haloalkane, known as the Williamson ether synthesis. He regarded ethers and alcohols as substances analogous to and built up on the same type as water, and he further introduced the water-type as a ...
18-Crown-6 can be synthesized by the Williamson ether synthesis using potassium ion as the template cation. Structure of nickel-aquo nitrate complex of the ligand derived from the templated trimerization of 2-aminobenzaldehyde. [5] The phosphorus analogue of an aza crown can be prepared by a template reaction. [6]
The two main mechanisms were the S N 1 reaction and the S N 2 reaction, where S stands for substitution, N stands for nucleophilic, and the number represents the kinetic order of the reaction. [4] In the S N 2 reaction, the addition of the nucleophile and the elimination of leaving group take place simultaneously (i.e. a concerted reaction).
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. [2] The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the ...
Usually phenol ethers are synthesized through the condensation of phenol and an organic alcohol; however, other known reactions regarding the synthesis of ethers can be applied to phenol ethers as well. Anisole (C 6 H 5 OCH 3) is the simplest phenol ether, and is a versatile precursor for perfumes and pharmaceuticals. [1]
The leaving group X in the organic partner is usually a halide, although triflate, tosylate, pivalate esters, and other pseudohalides have been used. [15] Chloride is an ideal group due to the low cost of organochlorine compounds.
For example, the synthesis of macrocidin A, a fungal metabolite, involves an intramolecular ring closing step via an S N 2 reaction with a phenoxide group as the nucleophile and a halide as the leaving group, forming an ether. [2] Reactions such as this, with an alkoxide as the nucleophile, are known as the Williamson ether synthesis.