Oxidative decarboxylation of the 3-methyl-2-carboxynorbornanes with lead tetraacetate

1976 ◽  
Vol 54 (8) ◽  
pp. 1222-1225 ◽  
Author(s):  
J. B. Stothers ◽  
K. C. Teo
Keyword(s):  
Carboxylic Acids ◽  
Lead Tetraacetate ◽  
Starting Material ◽  
Oxidative Decarboxylation ◽  
Methyl Group

The mixtures of isomeric acetates produced by oxidative decarboxylation of the four 3-methyl-norbornane-2-carboxylic acids with lead tetraacetate in benzene have been characterized. The composition of these products depends primarily on the configuration of the methyl group in the starting material. The results are compared with those found for the Pb(OAc)4 decarboxylation of the norbornane-, bornane-, and 2,3,3-trimethylnorbornane-2-carboxylic acids. The formation of the products is interpreted in terms of competitive cationic and SNi substitution.

Oxidative decarboxylation of some Bicyclo[4,1,0]hept-3-ene-1-carboxylic acids

1983 ◽  
Vol 36 (3) ◽  
pp. 593 ◽  
Author(s):  
N Galloway ◽  
BR Dent ◽  
B Halton
Keyword(s):  
Carboxylic Acids ◽  
Lead Tetraacetate ◽  
Oxidative Decarboxylation

Treatment of the bicyclo[4,1,0]hept-3-ene-1-carboxylic acids (8d-f) with lead tetraacetate results in oxidative decarboxylation and formation of the 1-aryl-1-methylethyl acetates (12a-c).

The mechanism of lead tetraacetate decarboxylation. II. 2,3,3-Trimethylbutanoic and Adamantane-2-carboxylic acids

1974 ◽  
Vol 27 (8) ◽  
pp. 1693 ◽  
Author(s):  
ALJ Beckwith ◽  
RT Cross ◽  
GE Gream
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Major Product ◽  
Lead Tetraacetate ◽  
Oxidative Decarboxylation ◽  
Catalysed Reaction

Oxidative decarboxylation of 2,3,3-trimethylbutanoic acid with lead tetraacetate in benzene or acetic acid affords mainly 3,3-dimethylbut-2-yl acetate; the major product from the cupric salt catalysed reaction is 3,3-dimethylbut-1-ene. The low yields detected of rearrangement products provide evidence for the intermediacy of organolead and organocopper compounds which decompose by SNi displacement or cyclic cis-elimination. Other reactions discussed are oxidative decarboxylation of adamantane-2-carboxylic acid, deamination of 3,3-dimethylbut-2-ylamine, and thermolysis of bis(2,3,3-trimethylbutanoyl) peroxide and of t-butyl adamantane-2-percarboxylate. A reinterpretation of previous results on the oxidative decarboxylation of exo- and endo-nor- bornane-2-carboxylic acid with lead tetraacetate is presented.

Exploring substrate scope and stereoselectivity of P450 peroxygenase OleTJEin olefin-forming oxidative decarboxylation

2016 ◽  
Vol 52 (52) ◽  
pp. 8131-8133 ◽  
Author(s):  
Jian-bo Wang ◽  
Richard Lonsdale ◽  
Manfred T. Reetz
Keyword(s):  
Carboxylic Acids ◽  
Oxidative Decarboxylation ◽  
Straight Chain

The substrate scope of the mild olefin-forming oxidative decarboxylation of straight-chain C4–C22carboxylic acids catalyzed by P450 peroxygenase OleTJEhas been extended to include structurally diverse carboxylic acids.

ChemInform Abstract: Iodosobenzene Diacetate, an Efficient Reagent for the Oxidative Decarboxylation of Carboxylic Acids.

1986 ◽  
Vol 17 (34) ◽  
Author(s):  
J. I. CONCEPCION ◽  
C. G. FRANCISCO ◽  
R. FREIRE ◽  
R. HERNANDEZ ◽  
J. A. SALAZAR ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Oxidative Decarboxylation ◽  
Efficient Reagent
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