Heterocyclic Synthesis by Persulphate Oxidation.
Final technical rept. 31 Oct 72-1 Nov 73,
ABERDEEN UNIV (SCOTLAND) DEPT OF CHEMISTRY
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Photolysis of a series of N-phenyl-C-o-carboxy-methoxyphenyl nitrones in the presence of persulphate yields the corresponding 2H-4-aryl-1,4-benzoxazin-3-ones as the principal products. Persulphate oxidation thermolysis and photolysis of o-carboxy-, o-carboxyamido- and o-anilinocarbonyl-phenoxyacetic acids yields mainly 1,3-benzodioxan-4-one. o-Phenylazo- and o-phenylazoxy-phenoxyisopropyl radicals generated from the corresponding aryloxy-acids show little tendency to cyclise intramolecularly. 2-Methylamino- and 2-ethylamino-1,4-naphthoquinones but not the t-butylamino homologue dimerise C3-C3 on oxidation with persulphate. The dimers are accompanied by the corresponding 9- alkyl02,36,7-dibenzocarbazole-1,45,8- diquinones. Mechanisms are discussed. Modified author abstract
- Organic Chemistry