Premium
Correlations of rate and selectivity of a Diels–Alder reaction with S p parameters
Author(s) -
Cativiela Carlos,
Mayoral Jose A.,
Avenoza Alberto,
Peregrina Jesus M.,
Roy Miguel A.
Publication year - 1990
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610030610
Subject(s) - chemistry , cyclopentadiene , selectivity , acetone , diels–alder reaction , organic chemistry , medicinal chemistry , computational chemistry , catalysis
The rate and endo / exo selectivity of the Diels–Alder reaction between cyclopentadiene and methyl ( E )‐α‐cyanocinnamate at 25°C, in several acetone–water and 1,4‐dioxane–water mixtures, were measured. The linear correlations of log k and log( endo / exo ) vs solvophobicity are reported. Correlations for selectivity are considerably improved when the results obtained in acetone–water and 1,4‐dioxane–water are taken as separate series.