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Allyl alcohol is converted mainly to glycidol, which is a chemical intermediate in the synthesis of glycerol, glycidyl ethers, esters, and amines. Also, a variety of polymerizable esters are prepared from allyl alcohol, e.g. diallyl phthalate. [5] Allyl alcohol has herbicidal activity and can be used as a weed eradicant [9]) and fungicide. [8]
The conversion of valencene to nootkatone is an example of allylic oxidation. In the synthesis of some fine chemicals, selenium dioxide is used to convert alkenes to allylic alcohols: [15] R 2 C=CR'-CHR" 2 + [O] → R 2 C=CR'-C(OH)R" 2. where R, R', R" may be alkyl or aryl substituents.
The Krische allylation involves the enantioselective iridium-catalyzed addition of an allyl group to an aldehyde or an alcohol, resulting in the formation of a secondary homoallylic alcohol. [1] [2] The mechanism of the Krische allylation involves primary alcohol dehydrogenation or, when using aldehyde reactants, hydrogen transfer from 2 ...
A variety of allylic ethers undergo the Wittig rearrangement—the fundamental requirement is the ability to generate the appropriate carbanion in the substrate. This demands either acidic hydrogens, a reducible functional group, or a carbon-metal bond. Historically, alkenyl, alkynyl, and phenyl groups have been used to acidify the α position ...
The Kharasch–Sosnovsky reaction is a method that involves using a copper or cobalt salt as a catalyst to oxidize olefins at the allylic position, subsequently condensing a peroxy ester (e.g. tert-Butyl peroxybenzoate) or a peroxide resulting in the formation of allylic benzoates or alcohols via radical oxidation. [1]
The Wharton olefin synthesis or the Wharton reaction is a chemical reaction that involves the reduction of α,β-epoxy ketones using hydrazine to give allylic alcohols. [1] [2] [3] This reaction, introduced in 1961 by P. S. Wharton, is an extension of the Wolff–Kishner reduction.
The Sharpless epoxidation has been used for the total synthesis of various saccharides, terpenes, leukotrienes, pheromones, and antibiotics. [ 6 ] The main drawback of this protocol is the necessity of the presence of an allylic alcohol .
Removal of a proton adjacent to the epoxide, elimination, and neutralization of the resulting alkoxide lead to synthetically useful allylic alcohol products. In reactions of chiral , non-racemic epoxides, the configuration of the allylic alcohol product matches that of the epoxide substrate at the carbon whose C–O bond does not break (the ...