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Type of Document	Dissertation
Author	Fort, Arthur W.
URN	etd-12122003-161659
Persistent URL	http://resolver.caltech.edu/CaltechETD:etd-12122003-161659
Title	The reaction of 3-arylpropylamines with nitric acid
Degree	PhD
Option	Chemistry
Advisory Committee	Advisor Name Title Prof. John D. Roberts Committee Member
Keywords	none
Date of Defense	1955-01-01
Availability	unrestricted
Abstract NOTE: Text or symbols not renderable in plain ASCII are indicated by [...]. Abstract is included in .pdf document. 3-Phenylpropylamine[...] reacts with nitrous acid in aqueous solution to give hydrocinnamyl alcohol, benzylmethylcarbinol and allylbenzene in the ratio 2.5:1.6:1.0. Under similar conditions, [...] gives[...]-methoxyhydrocinnamyl alcohol,[...] in the ratio 2.1:1.4:1.0. No evidence was found for the presence of other isomeric alcohols or olefins. A sample of each product from 3-phenylpropylamine-[...] was oxidized to benzoic acid, which was found to be inactive in each case. Likewise, anisic acid obtained from each of the products from [...].was found to be inactive. The number two carbon atom of each of the six products was shown to contain less than 0.5% of the total [...] activity of the product except in the case of benzylmethylcarbinol-[...], where the activity at C-2 was found to be 0-3%. These results eliminate the symmetrical carbonium ions having structures A and B as intermediates in the reactions studied. [...]
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