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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]
A site adjacent to the unsaturated carbon atom is called the allylic position or allylic site. A group attached at this site is sometimes described as allylic. Thus, CH 2 =CHCH 2 OH "has an allylic hydroxyl group". Allylic C−H bonds are about 15% weaker than the C−H bonds in ordinary sp 3 carbon centers and are thus more reactive.
Glycidol is prepared by the epoxidation of allyl alcohol.A typical catalyst is tungstic acid, and a typical O-atom source is aqueous peroxyacetic acid. [8]Some useful products derived from glycidol are 2,3-epoxypropyloxy chloroformate (from phosgene) and glycidyl urethanes (by addition of isocyanates: [8]
One workaround to avoid this method is to reduce the carboxylic acid derivative all the way down to an alcohol, then oxidize the alcohol back to an aldehyde. Other alternatives include forming a thioester or a Weinreb amide, then reducing the new species to an aldehyde through the Fukuyama reduction or Weinreb reaction respectively, or using ...
The Wharton olefin synthesis allows the transformation of an α,β unsaturated ketone into an allylic alcohol. The epoxide starting material can be generated by a number of methods, with the most common being reaction of the corresponding alkene with hydrogen peroxide or m-chloroperoxybenzoic acid. The Wharton reaction also commonly suffers ...
Chavicol is formed in sweet basil (Ocimum Basilicum) by the phenylpropanoid pathway via p-coumaryl alcohol. The allylic alcohol in p -coumaryl alcohol is converted into a leaving group. This then leaves thus forming a cation, this cation can be regarded as a quinone methide which then is reduced by NADPH to form either anol or chavicol.
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Carbonyl allylation has been employed in the synthesis of polyketide natural products and other oxygenated molecules with a contiguous array of stereocenters. For example, allylstannanation of a threose-derived aldehyde affords the macrolide antascomicin B, which structurally resembles FK506 and rapamycin, and is a potent binder of FKBP12. [12]