The reaction of 3-arylpropylamines with nitric acid

Citation

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

Abstract

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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.

[...]

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