A new form of secondary interaction in diels-alder reactions |
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Authors: | Yu E Raifel'd B S Él'yanov S M Makin |
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Institution: | (1) A.V. Topchiev Institute of Petrochemical Synthesis RAS, Leninskii prospect 29, 119991 Moscow, Russia |
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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- 3-dihydropyrans, corresponding to the endo-orientation of the diene and dienophile in the transition state.
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The observed effect is explained by the presence of interaction of the partially protonated hydrogen on the -carbon atom of the aldehyde with the -system of the diene.
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