The Journal of Organic Chemistry

Medium effects on formation of cyclic enolates from (2E, 4Z)-3-formyl-2, 4-hexadienedioates, a novel ring-chain equilibrium: importance of hydrogen bonding, solvent …

JW Jaroszewski, MG Ettlinger

Index: Jaroszewski, Jerzy W.; Ettlinger, Martin G. Journal of Organic Chemistry, 1989 , vol. 54, # 7 p. 1506 - 1518

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Citation Number: 8

Abstract

Medium effects on the cyclization equilibrium of the anion of 1-monomethyl (2E, 42)-3- formy1-2, 4-hexadienedioate, involving an intramolecular conjugate nucleophilic addition of a carboxylate ion to an a,@-unsaturated aldehyde moiety, were studied by UV spectroscopy. The s-transoid conformer of the a,@-unsaturated aldehyde cyclizes faster than the s-cisoid conformer, but at equilibrium the product of the latter cyclization predominates. The ...

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