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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]
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 ...
The mechanism starts with an allylic sulfoxide 1 which undergoes a thermal 2,3-sigmatropic rearrangement to give a sulfenate ester 2. This can be cleaved using a thiophile, such as phosphite ester , which leaves the allylic alcohol 3 as the product.
The Sharpless epoxidation is an example of an enantioselective process, in which an achiral allylic alcohol substrate is transformed into an optically active epoxyalcohol. In the case of chiral allylic alcohols, kinetic resolution results. Another example is Sharpless asymmetric dihydroxylation. In the example below the achiral alkene yields ...
Download as PDF; Printable version; In other projects ... Allyl alcohol or 2-propen-1-ol, ... Text is available under the Creative Commons Attribution-ShareAlike 4.0 ...
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.
An enone forms an allylic alcohol in a 1,2-addition, and the competing conjugate 1,4-addition is suppressed. The selectivity can be explained in terms of the HSAB theory: carbonyl groups require hard nucleophiles for 1,2-addition. The hardness of the borohydride is increased by replacing hydride groups with alkoxide groups, a reaction catalyzed ...
The Sharpless epoxidation is viable with a large range of primary and secondary alkenic alcohols. Furthermore, with the exception noted above, a given dialkyl tartrate will preferentially add to the same face independent of the substitution on the alkene.To demonstrate the synthetic utility of the Sharpless epoxidation, the Sharpless group created synthetic intermediates of various natural ...