Journal of the Chemical Society. Perkin transactions II p. 11 - 16 (1985)
Update date:2022-08-16
Topics:
El'yanov, Boris S.
Shakhova, Svetlana K.
Polkovnikov, Boris D.
Rar, Lev F.
A method of studying transition-state structures by analysis of volumetric steric effects is proposed.The method is used to reveal features of the steric structure of the transition state in Diels-Alder reactions.The structure has been found to change from one approximating the structure of the prereactional complex to that resembling the half-chair adduct as the diene substituent changes from methyl to t-butyl.As this takes place, no intermediate half-boat adduct is formed.An increase in steric hindrance during the change in the substituent is regarded as the driving force responsible for the transition-state shift along the reaction co-ordinate.This is consistent with the Hammond postulate.The C=O and C=C groups of the dienophile in the endo-transition state are in the s-cis-conformation.
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