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.

D-APIOSE

1958 ◽  
Vol 36 (3) ◽  
pp. 480-485 ◽  
Author(s):  
P. A. J. Gorin ◽  
A. S. Perlin
Keyword(s):  
Lead Tetraacetate ◽  
Open Chain ◽  
Naturally Occurring ◽  
Chain Form

Naturally-occurring apiose is shown by synthesis to be the D-isomer in the open-chain form. In this synthesis 3-O-benzyl-D-fructose is cyanohydrated and the resulting heptonic lactones are reduced to 3-O-benzyl-2-C-(hydroxymethyl)-D-arabo-hexitol. The latter is oxidized with lead tetraacetate affording 2-O-benzyl-3-C-(hydroxymethyl)-D-glycero-tetrose which, on debenzylation, gives 3-C-(hydroxymethyl)-D-glycero-tetrose (D-apiose).

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.

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