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Oxidative dimerization of 1,1-dimethyl-4-phenylsemicarbazide with lead tetraacetate: A novel route to the hexahydrotetrazine ring system

✍ Scribed by J.H. Cooley; J.W. Atchison Jr.

Publisher: Elsevier Science
Year: 1969
Tongue: French
Weight: 96 KB
Volume: 10
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)88720-7

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✦ Synopsis

The finding that 1-benzyloxy-3-phenylureas undergo oxidative ring closures with lead tetraacetate in chloroform to l-benayloxybenzimidazolones In nearly quantitative yields (1) caused us to extend the study to other systems containing a readily oxidizable group situated y with respect to an aromatic ring. Our first effort with phenoxyethanol was moderately successful and a 15% yield of benzodioxane* product was obtained. At this time Stames

(2) reported ring closed products from the lead tetraacetate oxidation of 3,3,3-triphenyl-lpropanol.

Because of this report our attention was turned to the oxidation of other systems.

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