A Stereochemical Study of the Basecatalyzed Decarboxylation of 4-tert-Butylcyclohexane-1,1-Dicarboxylic Acid
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Authors
Jacobs, William
Issue Date
1974-05
Type
Thesis
Language
en_US
Keywords
Chemistry , Stereochemistry
Alternative Title
Abstract
Base-catalyzed decarboxylation of 4-t-butylcyclohexane-1, 1-dicarboxylic acid using pyridine, 2-methylpyridine, 2,6-dimethylpyridine, 3,5-dimethylpyridine and N,N-dimethylaniline at 100.0 was investigated in terms of the stereochemistry of the product. In all bases, the major product was cis-4-t-butylcyclohexanecarboxylic acid. The product composition was rationalized in terms of differing selectivity for the two faces of the enediol intermediate, depending on the steric requirements of the proton donor. The results of a decarboxylation using dimethylformamide as solvent are also described.
Description
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Citation
W. Jacobs, "A Stereochemical Study of the Basecatalyzed Decarboxylation of 4-tert-Butylcyclohexane-1,1-Dicarboxylic Acid", MS dissertation, School of Arts & Sciences, Univ. of Bridgeport, Bridgeport, CT, 1974.