- Metal-Free Etherification of Aryl Methyl Ether Derivatives by C-OMe Bond Cleavage
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A general and efficient protocol was developed for the synthesis of aryl alkyl ethers through metal-free C-OMe bond cleavage under mild reaction conditions. This process displays a wide scope of methoxyarenes and alcohols, including primary, secondary, and tertiary alcohols, as well as natural products, pharmaceuticals, and biologically active alcohols. DFT calculations and experimental results simultaneously confirm that a potassium ion plays a critical role in the activation of methoxy group via binding with the nitrile and provide support for an SNAr mechanism.
- Wang, Xueqiang,Li, Chenchen,Wang, Xia,Wang, Qingli,Dong, Xiu-Qin,Duan, Abing,Zhao, Wanxiang
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supporting information
p. 4267 - 4272
(2018/07/29)
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- The ortho-substituent effect on the Ag-Catalysed decarboxylation of benzoic acids
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A combined experimental and computational investigation on the Ag-catalysed decarboxylation of benzoic acids is reported herein. The present study demonstrates that a substituent at the ortho position exerts dual effects in the decarboxylation event. On one hand, ortho-substituted benzoic acids are inherently destabilised starting materials compared to their meta- And para-substituted counterparts. On the other hand, the presence of an ortho-electron-withdrawing group results in an additional stabilisation of the transition state. The combination of both effects results in an overall reduction of the activation energy barrier associated with the decarboxylation event. Furthermore, the Fujita- Nishioka linear free energy relationship model indicates that steric bulk of the substituent can also exert a negative effect by destabilising the transition state of decarboxylation.
- Grainger, Rachel,Cornella, Josep,Blakemore, David C.,Larrosa, Igor,Campanera, Josep M.
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supporting information
p. 16680 - 16687
(2015/03/05)
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- Modulators (inhibitors/ activators) of histone acetyltransferases
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Disclosed are compounds of the formulae: and method of using the compounds to treat cancer, AIDS, HIV infection, and asthma.
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Page/Page column 4-5
(2008/06/13)
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- Pyrolysis of O-Allyl Salicylic Amides and Esters, and Related Compounds: Foemation of Isoindolones and Phthalides
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Flash vacuum pyrolysis of O-allyl salicylic alkylamides and alkyl esters gives isoindolones and phthalides, respectively, in low (20-40percent) yield.The mechanism involves generation of the phenoxyl radical, regiospecific hydrogen-atom transfer from the alkylamide (or alkyl ester) group and cyclization.A similar sequence was observed with thiophenoxyl radicals.
- Black, Michael,Cadogan, J. I. G.,McNab, Hamish
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p. 155 - 160
(2007/10/02)
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- Facile alkoxyl exchange of 2-methoxybenzoates via nucleophilic aromatic substitution with sodium alkoxides in dimethylformamide
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Methyl 2-methoxybenzoate undergoes facile nuclear-methoxyl displacement by treatment with sodium butexide or isopropoxide in dimethylformamide.
- Hattori,Satoh,Miyano
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p. 3840 - 3842
(2007/10/02)
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