Issue 14, 1984

Thermolysis of allene-1,1-dicarboxamides: acceleration of the intramolecular Diels–Alder reaction by intramolecular hydrogen bonding and a novel bicyclo[2.2.2]- to bicyclo[3.2.1]-alkadiene rearrangement

Abstract

Allene carboxanilides (5) with an additional geminal secondary carbamoyl group undergo intramolecular Diels–Alder reactions at rather low temperature (80 °C) to furnish the tricyclic lactams (6), which, in turn, isomerize to give the tricyclic lactams (8) at about 130 °C.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1984, 900-901

Thermolysis of allene-1,1-dicarboxamides: acceleration of the intramolecular Diels–Alder reaction by intramolecular hydrogen bonding and a novel bicyclo[2.2.2]- to bicyclo[3.2.1]-alkadiene rearrangement

G. Himbert, K. Diehl and G. Mass, J. Chem. Soc., Chem. Commun., 1984, 900 DOI: 10.1039/C39840000900

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