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Development of a model to explain the influence of the solvent on the rate and selectivity of diels–alder reactions
Author(s) -
Cativiela C.,
Garcia J. I.,
Mayoral J. A.,
Avenoza A.,
Peregrina J. M.,
Roy M. A.
Publication year - 1991
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.610040108
Subject(s) - chemistry , selectivity , cyclopentadiene , solvophobic , solvent effects , methyl acrylate , solvent polarity , solvent , acrylate , reagent , computational chemistry , diels–alder reaction , cyclopentene , organic chemistry , catalysis , copolymer , polymer
Solvophobic and polarity parameters are used to explain the endo/exo selectivity of the reaction between cyclopentadiene and methyl acrylate. A good linear regression model with Sp and E T Nis obtained. The existence of an intrinsic correlation between the Sp and E T Nvalues, which makes the interpretation of the results difficult, is shown. A comparison of the results with other previously reported showed that the relative influence of Sp and E T Non selectivity depends on the nature of the reagents.