Solvent effects on the 9-hydroxymethylanthracene + N-ethylmaleimide Diels-Alder reaction. A theoretical study.
J Org Chem
; 70(4): 1456-8, 2005 Feb 18.
Article
in En
| MEDLINE
| ID: mdl-15704984
ABSTRACT
[structure see text] The origin of the high reaction rates of the 9-hydroxymethylanthracene + N-ethylmaleimide Diels-Alder reaction in fluorous solvents and supercritical carbon dioxide is analyzed through a combination of regression analyses and theoretical calculations. Both approaches allow the solvent effects on the activation barrier (a decrease by solvophobic interactions, an increase by dipolarity-polarizability) to be attributed to the existence of a hydrogen bond between the two reactants in the transition state, refuting a previous hypothesis based on strong solvophobic interactions.
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Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
J Org Chem
Year:
2005
Document type:
Article
Affiliation country:
Spain