Journal of the Chemical Society. Perkin transactions I p. 1695 - 1698 (1996)
Update date:2022-08-30
Topics:
Crombie, Leslie
Dove, Roderick V.
The structure, and mechanism of formation, of the pyrone-glutaconic anhydride (GP1) obtained by treatment of diaikylxanthophanic enols with concentrated H2SO4 or F3CCO2H, is further supported, and a new example GP2 is prepared. Experiments with deuteriated acids show that deuterium is introduced at C-5′ and the unchelated acetyl of GP1, the second acetyl being apparently protected by chelation. This is supported by benzenoid test examples, though in the naphthalene series acetyl migration also occurs through deacylation/reacylation. An explanation of the protective effect of chelation against acid catalysed enolisation of the acetyl methyl is suggested.
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