
%0 Journal Article
%A Beckwith, ALJ 
%A Cross, RT 
%A Gream, GE 
%T The mechanism of lead tetraacetate decarboxylation. II. 2,3,3-Trimethylbutanoic and Adamantane-2-carboxylic acids
%J Australian Journal of Chemistry
%D 1974/08/01
%V 27
%N 8
%P 1693-1710
%K 
%R https://doi.org/10.1071/CH9741693
%U https://www.publish.csiro.au/paper/CH9741693 
%X 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. 
