Flash vacuum pyrolysis of the diethyl esters 2 gives 2-ethynylpyrrole via the anhydride 7; the corresponding dimethyl esters 3 give, under similar conditions, the pyrrolizinone 5, which is remarkably unstable and spontaneously dimerises to give the [2 + 2] cycloadducts 8 and 9 whose structures are proved by X-ray crystallography.
M. C. Comer, X. L. M. Despinoy, R. O. Gould, H. McNab and S. Parsons, Chem. Commun., 1996, 1083 DOI: 10.1039/CC9960001083
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