Health & Environmental Research Online (HERO)


Print Feedback Export to File
8412363 
Journal Article 
The Electrolytic Decarboxylation of cis- and trans-Bicyclo [3.1.0] hexane-3-carboxylic Acids 
Gassman, PG; Zalar, FV 
1966 
Yes 
Journal of the American Chemical Society
ISSN: 0002-7863
EISSN: 1520-5126 
88 
10 
2252-2257 
English 
The electrolytic oxidative decarboxylation of cis- and trans-bicyclo[3.1.0]hexane-3-carboxylic acid was investigated. When the electrolysis was run in pyridine-water the predominant products were cis- and trans-bicyclo[3.1.0]hexan-2-ols. These rearranged alcohols are explained on the basis of cationic intermediates. The reactions are stereospecific insofar as the trans acid yields mostly trans alcohol while the cis acid yields cis alcohol as the major product. Bicyclo[3.1,0]hexane-3-carboxylic acid labeled with deuterium at C-6 was converted to bicyclo-[3.1.0]hexan-2-ols with no deuterium shift. These results are discussed in relation to the question of the existence of trishomocyclopropenyl cations. © 1966, American Chemical Society. All rights reserved.