Issue 15, 1973

Relative reactivities and activation parameters for the Vilsmeier–Haack formylation of five-membered heteroaromatic compounds containing the Group VI elements

Abstract

Rate constants and activation parameters are determined for the formylation by the HCONMe2–COCl2 complex in CHCl3, of furan, thiophen, selenophen, and tellurophen. ΔS Values are identical within experimental error, and the reaction is enthalpy controlled. The activation entropies are discussed in terms of the position of the transition states along the reaction co-ordinate, whereas ΔH values are correlated with ‘empirical resonance energies’ and ΔEloc. The results indicate that the transition states for all four compounds lie in a similar position along the reaction co-ordinate and that the differences in ground state energy play a fundamental role in determining the relative reactivities of the α-positions.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1973, 2097-2100

Relative reactivities and activation parameters for the Vilsmeier–Haack formylation of five-membered heteroaromatic compounds containing the Group VI elements

S. Clementi, F. Fringuelli, P. Linda, G. Marino, G. Savelli and A. Taticchi, J. Chem. Soc., Perkin Trans. 2, 1973, 2097 DOI: 10.1039/P29730002097

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