Collect. Czech. Chem. Commun. 1983, 48, 96-102

Reaction of substituted γ-crotonolactones under the conditions of the Michael addition

Miroslav Janda, Eva Körblová and Ivan Stibor

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Under the conditions of the Michael addition γ-lactone of ethyl 4-hydroxy-6-oxo-2-octenedioate (II) isomerizes to γ-lactone of ethyl 4-hydroxy-6-oxo-4-octenedioate (VIII). The addition of an excess of ethyl acetate anion to γ-lactone of ethyl 4-hydroxy-2-hexenedioate (I) affords γ-lactone of ethyl 3-ethoxycarbonylmethyl-4-hydroxy-6-oxo-octanedioate (XI). The dimers IX and X are formed during the usual performance of the same addition. The mechanism of isomerization of II and the factors affecting the addition of the ethyl acetate anion are discussed.