J. Christoffers, A VINYLOGOUS DONOR IN AN IRON(III)-CATALYZED MICHAEL REACTION AND AN ENONE-DIENOL TAUTOMERISM, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (5), 1998, pp. 759-761
A double acceptor-activated cycloalkene 1 reacts in an FeCl3 . 6 H2O c
atalysed Michael reaction surprisingly as a donor. The constitution of
the product 2 results from a reaction of 1 in the gamma-position, thu
s the Michael reaction is vinylogous with respect to the donor. A taut
omerism between the enone 1 and the dienol 4 is found to be a precondi
tion for this reactivity.