Part I. cis- and trans-l,2-Diaminocyclohexanes. Part II. A Study of the Tertiary Amine Precursors of Pirylene

Citation

Farrar, Grover Louis (1961) Part I. cis- and trans-l,2-Diaminocyclohexanes. Part II. A Study of the Tertiary Amine Precursors of Pirylene. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/F20M-YA16. https://resolver.caltech.edu/CaltechETD:etd-03282006-131742

Abstract

PART I: cis- and trans-1,2-Diaminocyclohexanes: Work initiated in these laboratories by Reims and Buchman on the stereospecific conversion of cis- and trans-cyclohexane-1,2-dicarboxylic acids to the corresponding diamines has been extended. cis- and trans-1,2-Diaminocyclohexanes have been characterized by measurements of densities, refractive indices, acid constants and melting points and by preparations of both side-chain and cyclic derivatives. PART II: A study of the tertiary amine precursors of pirylene: The observation of Sargent, Buchman and Farquhar, that the Hofmann degradation of N,N-dimethyl-[alpha]-bromomethylpyrrolidinium bromide does not give a single C7H13N amine, but a mixture of isomeric tertiary amines has been confirmed. The components of the C7H13N amine mixture have been identified as follows: (1) 1-dimethylamino-4-pentyne (2) 1-dimethylamino-2,4-pentadiene (3) 1-dimethylamino-3,4-pentadiene (4) 1-dimethylamino-3-pentyne (5) 1-dimethylamino-1,3-pentadiene. Components (2), (4) and (5) have been isolated and characterized. Components (1) and (3) were detected by infrared spectroscopy. A probable course of formation of the C7H13N amine mixture from N,N-dimethyl-[alpha]-bromomethylpyrrolidinium bromide is discussed.

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