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Cycloadditions, 12. - Influence of Aromatic Alkyl Groups on the Intramolecular Diels-Alder Reaction of Aryl Allenecarboxylates and of Allenecarboxanilides
Himbert, Gerhard,Fink, Dieter,Diehl, Klaus
, p. 431 - 442 (2007/10/02)
The aryl allenecarboxylates 4a-o and the allenecarboxanilides 9a, b, e, h, and l, which differ from one another only by the number or by the size of the alkyl groups attached to the arene, are synthesized by the ylide method via the appropriately substituted 2-halo-, 2-phosphonio-, and 2-phosphoranylideneacetic acid derivatives (1-->2-->3-->4 and 6-->7-->8-->9, resp.).By refluxing in xylene they are transformed into the tricyclic compounds 5 and 10; the rates and their differences are discussed.
