102235-85-8Relevant articles and documents
Cycloadditions, 7. Intramolecular Diels-Alder Reactions of Allenecarboxanilides; Variation of the Substituents in the p-Position of the Aniline Nucleus
Diehl, Klaus,Himbert, Gerhard,Henn, Lothar
, p. 2430 - 2443 (2007/10/02)
The N-methyl-1,2-propadiene-1-carboxanilides 6a-h, differently substituted in the p-position, are synthesized by Wittig reaction of the carbamoylmethylenephosphoranes 5 with ketene.They isomerize by thermolysis in boiling xylene to give the tricycles 7a-h, the products of the intramolecular Diels-Alder reaction, and in some cases also to the quinolones 9, the products of a cyclization reaction.The order of the reaction and the influence of the substituents upon the rate of the intramolecular Diels -Alder reaction are determined by 1H-NMR spectroscopy.