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A new form of secondary interaction in diels-alder reactions
Authors:Yu E Raifel'd  B S Él'yanov  S M Makin
Institution:(1) A.V. Topchiev Institute of Petrochemical Synthesis RAS, Leninskii prospect 29, 119991 Moscow, Russia
Abstract:
1.  The diene condensation of 1-alkoxy-1,3-butadienes with aliphatic aldehydes at high pressures leads to predominate formation of 2-alkoxy-6-alkyl-Delta3-dihydropyrans, corresponding to the endo-orientation of the diene and dienophile in the transition state.
2.  The observed effect is explained by the presence of interaction of the partially protonated hydrogen on the agr-carbon atom of the aldehyde with the pgr-system of the diene.
Keywords:
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