Acyloin Condensation-Name reaction
The acyloin condensation usually involves the reductive dimerization of a carboxylic ester, although acid chlorides and the anhydrides have been used. The reducing agent is in an alkali metal and the product is an ene-diolate. Two gram-atoms of metal are required for each mole of ester with the concomitant formation of a mole of akoxide and one-half mole of the ene-diolate. Oxidation of acyloins to diketoes can be accomplished by a variety of reagents. Acyloins can be reduced to ketones by various modifications of the Clemmenson technique. Under mild conditions the ketone will dominate. This chapter presents a complete picture of both the linear and cyclic acyloin condensation with particular emphasis on developments since 1960. The discussion is closely limited to the acyloin condensation and its modifications
Acyloin condensation is a reductive coupling of two carboxylic esters using metallic sodium to yield an α-hydroxyketone, also known as an acyloin
Mechanism of Acyloin Condensation
Books related to Acyloin Condensation
1.March’s Advanced Organic Chemistry: Reactions, Mechanisms, and StructureHardcover – April 22, 2013 by Michael B. Smith
3.Acyloin Condensation examples (More)
Esters undergo a dimerization reduction reaction that is called an acyloin condensation. This name comes from the common name of the simplest reaction product, acyloin, which is an α-hydroxy
ketone. The initial product of the reaction is the disodium salt of an enediol. To form the acyloin product, the disodium salt hydrolyzes in aqueous acid.
- Bouveault, L., and R. Loquin (1905). “Action du sodium sur les éthers des acides monobasiques à fonction simple de la série grasse”. Compt. Rend. 140: 1593–1595.
- Finley, K. T. (1964). “The Acyloin Condensation as a Cyclization Method”. Chemical Reviews 64 (5): 573–589. doi:10.1021/cr60231a004.
- Bloomfield, J. J.; Owsley, D. C.; Nelke, J. M. Org. React. 1976, 23.Acyloin condensation
- Rühlmann K. (1971). “Die Umsetzung von Carbonsäureestern mit Natrium in Gegenwart von Trimethylchlorsilan” [Reaction of carboxylic acid esters with sodium in the presence of trimethylchlorosilane Synthesis 1971
- Acyloin Ester Condensation(File PDF)
- Chemistry 144 Organic Synthesis M. E. Jung
- Preparation of cyclic acyloins – This condensation has been used for preparation cyclic acyloins. Long chain dicarboxylic esters have been converted to large ring compounds without the use of dilution technique. It is used best for closing rings of ten members or more.
- Preparation of CATENANE – CATENANE is a very interesting & unique compound with interlocking rings. It is formed when acyloin condensation was employed for ring closure with esters of 34-carbon dicarboxylic acids.