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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]
One commercial application of allylic oxidation is the synthesis of nootkatone, the fragrance of grapefruit, from valencene, a more abundantly available sesquiterpenoid: [14] The conversion of valencene to nootkatone is an example of allylic oxidation.
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]
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 ...
When an α,β-unsaturated carbonyl is reduced, three products can result: an allyl alcohol from simple carbonyl reduction, a saturated ketone or aldehyde resulting from 1,4‑reduction (also called conjugate reduction), or the saturated alcohol from double reduction. [19]
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.
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]
Amyl alcohol isomers; Common name Structure Type IUPAC name Boiling point (°C) [3] 1-pentanol or normal amyl alcohol primary Pentan-1-ol: 138.5 2-methyl-1-butanol or active amyl alcohol primary 2-Methylbutan-1-ol: 128.7 3-methyl-1-butanol or isoamyl alcohol or isopentyl alcohol primary 3-Methylbutan-1-ol: 131.2 2,2-dimethyl-1-propanol or ...