Accession Number:

AD0770432

Title:

Heterocyclic Synthesis by Persulphate Oxidation.

Descriptive Note:

Final technical rept. 31 Oct 72-1 Nov 73,

Corporate Author:

ABERDEEN UNIV (SCOTLAND) DEPT OF CHEMISTRY

Personal Author(s):

• Thomson,R. H.

Report Date:

1973-10-31

Pagination or Media Count:

23.0

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- alkyl02,36,7-dibenzocarbazole-1,45,8- diquinones. Mechanisms are discussed. Modified author abstract

Descriptors:

• *ORGANIC NITROGEN COMPOUNDS
• *HETEROCYCLIC COMPOUNDS
• AROMATIC COMPOUNDS
• QUINONES
• SULFATES
• OXIDATION
• SYNTHESIS(CHEMISTRY)
• CHEMICAL REACTIONS
• UNITED KINGDOM
• PHOTOLYSIS
• PYROLYSIS
• ACETIC ACID
• FREE RADICALS

Subject Categories:

• Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE