ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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  σ_р(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 σ_р(Х-С₄Н₂О) constants are also reported.

Full paper in Portable Document Format: 283a386.pdf

Chemical Papers 28 (3) 386–390 (1974)