Issue 12, 1975

Substituent and solvent effects on the Diels–Alder reactions of triazolinediones

Abstract

The kinetics and activation parameters for the series of 4-substituted (R) 1,2,4-triazoline-3,5-diones (R = Me, Et, But, CH2Ph, Ph, p-MeOC6H4, p-NO2C6H4, or N:CHPh) have been measured for the Diels–Alder reactions with diphenylbutadiene, anthracene, hexachlorocyclopentadiene, and bicyclo[2.2.1]heptadiene. The reactions have been studied in benzene, dioxan, and ethyl acetate. The results are more in accord with the frontier orbital model of reactivity in the Diels–Alder reaction than with a standard linear free-energy approach.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1975, 1325-1334

Substituent and solvent effects on the Diels–Alder reactions of triazolinediones

M. E. Burrage, R. C. Cookson, S. S. Gupte and I. D. R. Stevens, J. Chem. Soc., Perkin Trans. 2, 1975, 1325 DOI: 10.1039/P29750001325

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