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| - Influence of Hydrogen Bonding in the Activation of Nucleophiles: PhSH−(Catalytic) KF in N-Methyl-2-pyrrolidone as an EfficientProtocol for Selective Cleavage of Alkyl/Aryl Esters and Aryl AlkylEthers under Nonhydrolytic and Neutral Conditions
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| - The nucleophilicity of arenethiols can be augmented via hydrogen bonding with ‘naked' halide anion.The activity of the halide anions follow the order F- ≫ Cl- ∼ Br- ∼ I- and is dependent on thecountercation (Bu4N ∼ Cs ∼ K > Na ≫ Li). The solvent plays an important role in nucleophilicactivation as well as regeneration of the effective nucleophile (e.g. ArS-) and those with highdielectric constant, high molecular polarizability, high donor number (DN), and low acceptor number(AN) are the most effective. Selective deprotection of alkyl/aryl esters and aryl alkyl ethers can beachieved under nonhydrolytic and neutral conditions by the treatment with thiophenol in 1-methyl-2-pyrrolidone (NMP) in the presence of a catalytic amount of KF. Aryl esters are selectivelydeprotected in the presence of alkyl esters and alkyl methyl ethers during intramolecularcompetitions.
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