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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 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 ...
Structure of the allyl group. In organic chemistry, an allyl group is a substituent with the structural formula −CH 2 −HC=CH 2. It consists of a methylene bridge (−CH 2 −) attached to a vinyl group (−CH=CH 2). [1] [2] The name is derived from the scientific name for garlic, Allium sativum.
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]
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]
An allylic rearrangement or allylic shift is an organic chemical reaction in which reaction at a center vicinal to a double bond causes the double bond to shift to an adjacent pair of atoms: It is encountered in both nucleophilic and electrophilic substitution , although it is usually suppressed relative to non-allylic substitution.
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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 ...