I. Contribution to the Stereochemistry of Stilbenes by Application of Chromatographic Methods. II. Separation of Some Cis- and Trans-Oximes by Means of the Chromatographic Brush Method. III. Chromatographic Isolation of Homopterocarpin and Vanillin from Red Sandalwood. IV. Model Experiments Directed Toward the Synthesis of Quinine

Citation

McNeely, William Harold (1943) I. Contribution to the Stereochemistry of Stilbenes by Application of Chromatographic Methods. II. Separation of Some Cis- and Trans-Oximes by Means of the Chromatographic Brush Method. III. Chromatographic Isolation of Homopterocarpin and Vanillin from Red Sandalwood. IV. Model Experiments Directed Toward the Synthesis of Quinine. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/R6H2-GN02. https://resolver.caltech.edu/CaltechTHESIS:02012017-104146897

Abstract

Part I.

The chromatographic brush method, with permanganate as brush reagent, has been used for the detection, separation and estimation of the cis- and trans-forms of stilbene, p-methylstilbene and p-methoxystilbene. In a mixture composed of two stereoisomeric compounds, 1-2% of either form can be detected. The method can be used for the study of the interconversion of stilbene cis- and trans-isomers. Fluorescent contaminants can be removed by chromatography in ultraviolet light.

Part II.

The chromatographic brush method, with an ammoniacal copper solution as color reagent, has been used for the detection and separation of cis- and trans-benzoin and anisoin oximes on Neutrol Filtrol columns. In a mixture composed of two stereoisoraers, 1-2% of either form can be rapidly detected in the presence of the other. Some data concerning the interconversion of stereoisomeric oximes is given, and the influence of the adsorbent on the cis-trans shift is discussed.

Part III.

A preliminary chromatographic investigation of some colorless constituents of red sandalwood has been carried out. The chromatographic isolation and purification of homopterocarpin and vanillin is described

Part IV.

Model experiments directed towards the synthesis of quinine have been carried out.

Thesis Files