Fort, Arthur W. (1955) The reaction of 3-arylpropylamines with nitric acid. Dissertation (Ph.D.), California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-12122003-161659
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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.
|Item Type:||Thesis (Dissertation (Ph.D.))|
|Degree Grantor:||California Institute of Technology|
|Division:||Chemistry and Chemical Engineering|
|Thesis Availability:||Public (worldwide access)|
|Defense Date:||1 January 1955|
|Default Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Imported from ETD-db|
|Deposited On:||17 Dec 2003|
|Last Modified:||26 Dec 2012 03:13|
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