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Type of Document	Dissertation
Author	Farrar, Grover Louis
URN	etd-03282006-131742
Persistent URL	http://resolver.caltech.edu/CaltechETD:etd-03282006-131742
Title	Part I: Cis- and trans-1,2-diaminocyclohexanes. Part II: A study of the tertiary amine precursors of pirylene
Degree	PhD
Option	Chemistry
Advisory Committee	Advisor Name Title Edwin Raphael Buchman Committee Chair George Simms Hammond Committee Member
Keywords	none
Date of Defense	1961-01-01
Availability	unrestricted
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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