Pyrolytic cyclisation reactions of 3-azolylpropenyl alcohols; unexpectedly facile thermal decomposition of 5 H-pyrrolo [2, 1-a] isoindole

…, H McNab, CC Sommerville, E Stevenson

Index: Clark, Bernard A. J.; Despinoy, Xavier L. M.; McNab, Hamish; Sommerville, Craig C.; Stevenson, Elizabeth Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 15 p. 2049 - 2051

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Abstract

Flash vacuum pyrolysis (FVP) of 3-azolylpropenyl alcohols 5–7, 12 or 15 at 650–700° C (10– 2–10–3 Torr) causes loss of water and cyclisation to give 3H-pyrrolizine 8 and its analogues 9, 10, 13 and 16; at higher temperatures (eg 900° C) 5H-pyrrolo [2, 1-a] isoindole 13 decomposes by loss of HCN to give naphthalene 18 and benzofulvene 19 and the mechanism of this transformation is studied by deuterium labelling.