Studies Relating to the Free Radical Chlorination of Cyclobutanecarboxylic Acids

Citation

Nevill, William Albert (1954) Studies Relating to the Free Radical Chlorination of Cyclobutanecarboxylic Acids. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/B3J7-0627. https://resolver.caltech.edu/CaltechETD:etd-12052003-092441

Abstract

The halogenated cyclobutanecarboxylic acid are of importance in connection with projected syntheses of theoretically important cyclobutane derivatives. To facilitate the direct synthesis of such compounds, the free radical chlorination of two simple models, cyclobutanecarboxylic acid and 1,1-cyclobutanedicarboxylic acid, has been investigated. Necessary to this study was the synthesis, by means indicative of structure, of 5 isomeric monochlorocyclobutanecarboxylic acids. A chromatographic method has been developed capable of effecting the separation of these isomers from a mixture. The results obtained in this work are consistent with modern interpretations of organic chemistry theory and extend the scope of its application in the field of free radical chlorination to carboxyl-substituted carbocyclic systems.

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