Remote intramolecular functionalization of arylnitrenium ions. ipso-substitution and spiro-lactone formation

Abstract
Acid-catalysed decomposition of (4′-azidophenyl)propanoic and butyric acids leads to ipso-attack by the carboxy group para to the nitrenium ion and the formation of imines of cyclohexadienone spiro-lactones, which can rearrange to the benz-fused lactones; 4′-azido-2-carboxydiphenyl ether behaves the same way to give spiro-lactone (9).

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