Citation
Fort, Arthur W. (1955) The reaction of 3-arylpropylamines with nitric acid. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/PCT4-DB71. https://resolver.caltech.edu/CaltechETD:etd-12122003-161659
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.
[...]
Item Type: | Thesis (Dissertation (Ph.D.)) |
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Degree Grantor: | California Institute of Technology |
Division: | Chemistry and Chemical Engineering |
Major Option: | Chemistry |
Thesis Availability: | Public (worldwide access) |
Research Advisor(s): |
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Thesis Committee: |
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Defense Date: | 1 January 1955 |
Record Number: | CaltechETD:etd-12122003-161659 |
Persistent URL: | https://resolver.caltech.edu/CaltechETD:etd-12122003-161659 |
DOI: | 10.7907/PCT4-DB71 |
Default Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. |
ID Code: | 4961 |
Collection: | CaltechTHESIS |
Deposited By: | Imported from ETD-db |
Deposited On: | 17 Dec 2003 |
Last Modified: | 21 Dec 2019 04:11 |
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