SOME 5,5′-FREE PYRROKETONES

1962 ◽  
Vol 40 (8) ◽  
pp. 1585-1589 ◽  
Author(s):  
J. M. Osgerby ◽  
S. F. MacDonald
Keyword(s):  
Acetic Acid ◽  
Lead Dioxide ◽  
Lead Tetraacetate

5,5′-Dicarbethoxypyrromethanes are oxidized to the pyrroketones by lead tetraacetate–lead dioxide in acetic acid. The 5,5′-free pyrroketones obtained by decarboxylating the latter have not yet proved synthetically useful.

Lead Tetraacetate Oxidations in the Sugar Group. V.1The Rates of Oxidation of Open-Chain Polyalcohols in Dry Acetic Acid Solution2

1944 ◽  
Vol 66 (3) ◽  
pp. 467-468 ◽  
Author(s):  
Robert C. Hockett ◽  
Margaret T. Dienes ◽  
Hewitt G. Fletcher ◽  
Hugh E. Ramsden
Keyword(s):  
Acetic Acid ◽  
Lead Tetraacetate ◽  
Open Chain ◽  
Group V

Improved synthesis of anti-sesquinorbornene

1984 ◽  
Vol 62 (9) ◽  
pp. 1840-1844 ◽  
Author(s):  
Karl R. Kopecky ◽  
Alan J. Miller
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Lead Tetraacetate ◽  
Carboxyl Group ◽  
Silver Acetate ◽  
Benzenesulfonyl Chloride ◽  
Methoxide Ion ◽  
Hydrolysis Of ◽  
Monomethyl Ester

Treatment of methyl hydrogen decahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a,8a-dicarboxylate with lead tetraacetate in benzene – acetic acid replaces the carboxyl group by an acetoxy group. Hydrolysis of this product with 25% sulfuric acid at 130 °C forms 8a-hydroxydecahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a-carboxylic acid 10. The reaction between 10 and benzenesulfonyl chloride in pyridine containing triethylamine at 95 °C produces anti-sesquinorbornene 1 in 34% yield. In the absence of triethylamine 1 is converted to the hydrochloride. The iodohydroperoxide of 1 is converted by silver acetate at 0 °C to the diketone in a luminescent reaction. The 1,2-dioxetane could not be isolated. Decahydro-1,4:5,8-exo,exo-dimethanonaphthalene-4a,8a-dicarboxylic anhydride is converted slowly by methoxide ion in methanol at 150 °C to the monomethyl ester which then undergoes demethylation. The isomeric exo,endo anhydride undergoes reaction readily with methoxide ion at 80 °C.

Sign in / Sign up

Export Citation Format

Share Document