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Furan derivatives. LVIII. Transfer of a substituent effect through the furan-benzene system. Alkaline hydrolysis of methyl esters of 4-(5-X-2-furyl)benzoic acids

Ľ. Fišera, J. Kováč, M. Lucký, and J. Surá

Department of Organic Chemistry, Slovak Technical University, 880 37 Bratislava


Abstract:  Some substituted 2-X-5-(4-methoxycarbonylphenyl)furans, where X = H, СНз, C2H5 , HOCH2, CHO, Br, I, CH3CO, NC, 02N, and CH3OOC, were prepared. The rate constants of alkaline hydrolysis of the prepared derivatives in 6 0% acetone at 25°C were determined and correlated with Hammett constants ( ρ = 1.056) and  σр(Х-С4Н20) constants (ρ = 2.854). The found values of the rate constants are discussed in connection with a transfer of the substituent effect through the furan — benzene system. Correlations of the shifts of the CO stretching frequencies of methyl esters in the i.r. spectra with the σр(Х-С4Н2О) constants are also reported.

Full paper in Portable Document Format: 283a386.pdf


Chemical Papers 28 (3) 386–390 (1974)

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