Internuclear cyclisation. Part XXIV. Catalysed decomposition of diazonium fluoroborates from amino-N-methyl-naphthanilides and -N-naphthylbenzamides

Abstract

Previously unidentified products formed in the catalysed decomposition of diazonium fluoroborates from amino-N-methyl-naphthanilides and -N-naphthylbenzamides are shown to include unsaturated spiro-dimers [(IV), (VI), (IX), (XIII), and (XV)], and a spiro-cyclohexadienone (III) in which an oxygen atom has been incorporated into the molecule. Products of deamination and demethylation and of normal ring closure are also formed but phthalimidines are not.