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Communication | Regular issue | Vol 19, No. 2, 1982, pp.265-271
Published online, 1st January, 1970
DOI: 10.3987/R-1982-02-0265
On the Synthetic Utility of Thermally Generated Imines: The Retro-Ene Imino Diels-Alder Reaction

Richard A. Earl and K. Peter C. Vollhardt

*Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, U.S.A.


The flash vacuum pyrolysis of several allyl and propargyl amines provides a preparatively useful synthesis of imines by retro-ene fragmentation. Their synthetic potential is indicated by intramolecular Diels-Alder trapping to give indolizidines in a novel ring-expansion sequence.