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Various polyfunctional oximes chelate with metals pro vided that the other functional group is proximal to the oxime and contains a good donor atom or is a good donor itself. Thus α-oximinocarboxamides are potential chelating agents of analytical value since the amide function attached to the carbon atom bearing the oxime has two groups capable of functioning as donors (ketone and amine). Two isomers of α-oximinophenylacetamide (AOPA) were obtained by two different synthetic routes, and structures were assigned by spectrometric methods. syn-AOPA was found to have chelating properties, but the anti-isomer did not. The synthesis and details of structure assignments are reported here.

2-Alkoxyiminoalkylmercaptans were treated with appropriate reagents by established procedures to prepare the corresponding “Bunte salts,” 2-(2-alkoxyiminoalkylthio)-2-imidazolines, 2-(2-alkoxyimino)alkyl dithiocarbonates, and ethyl 2-alkoxyiminoalkyl trithiocarbonates. Selected compounds were screened for radioprotective activity, and none was found to have significant activity.

2-Alkoxyiminoalkylmercaptans were treated with appropriate reagents by established procedures to prepare the corresponding “Bunte salts,” 2-(2-alkoxyiminoalkylthio)-2-imidazolines, 2-(2-alkoxyimino)alkyl dithiocarbonates, and ethyl 2-alkoxyiminoalkyl trithiocarbonates. Selected compounds were screened for radioprotective activity, and none was found to have significant activity.

Of three α -alkyloximinonitriles tested for radiation protection, two were very toxic and inactive, while one with low toxicity gave slight protection.

A preparation of α -alkyloximinonitriles is described in which the corresponding α -alkyloximinocarboxamides are heated with phosphorus pentoxide in vacuo . Structures were proven by infrared analysis and basic hydrolysis of the nitriles to the corresponding acids.

O -Alkylamidoximes were prepared by treatment of α -alkyloximinocarboxamides with sodium hypobromite. Of the five prepared, two have not been previously reported and one was reported as being an unstable oil. Structures were proven by NMR and nitrogen analysis.

New derivatives of α-alkyloximino acids, the thiol esters, were prepared by modification of an application of mixed carboxylic-carbonic anhydrides. In general, the compounds show modest antimalarial activity, though one prolongs the lives of infected mice for more than 3 days longer than controls.

Syn-alpha-oximinophenylacetamide forms two complexes with Cu(II), a CuL complex at pH8.4 and CuL(2) at pH8.4. log K(1) = 7.82 +/- 0.07 log beta(2) = 14.32 +/- 0.06.

N- β -Phenethyl amides of α -benzyloximino acids were prepared as intermediates for an attempted cyclization to the corresponding 3,4-dihydroisoquinoline derivatives.