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Influence of diene substitution on transition state stabilization in Diels-Alder reaction
Raphaël Robiette1, Jaqueline Marchand-Brynaert, Daniel Peeters
1Unité de Chimie structurale et des mécanismes réactionnels and Unité de Chimie organique et médicinale, Université catholique de Louvain Place L. Pasteur 1, B-1348 Louvain-la-Neuve, Belgium.
Abstract:
A theoretical analysis of transition state stabilization in D-A reactions of substituted dienes according to the nature and position of the substituent has been carried on. Results revealed that substituents (de)stabilize TS through four effects (steric, mesomeric, inductive, and polarizability) acting principally by favoring the electronic transfer between the two partners. The correlations observed point out nevertheless that the reactivity of substituted dienes in [4 + 2] cycloadditions on ethylene may principally be predicted by the sole use of the F + R electronic parameters.