Heterocyclic Synthesis by Persulphate Oxidation.
Abstract
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- alkyl02,3:6,7-dibenzocarbazole-1,4:5,8- diquinones. Mechanisms are discussed. (Modified author abstract)
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 31, 1973
- Accession Number
- AD0770432
Entities
People
- R. H. Thomson
Organizations
- University of Aberdeen