Substituent and solvent effects on the Diels–Alder reactions of triazolinediones
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 12,p. 1325-1334
- https://doi.org/10.1039/p29750001325
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.Keywords
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