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Timothy W Wallace

Publications and source records attributed to Timothy W Wallace.

3 recordsLinked to original sources

Biaryl synthesis with control of axial chirality.

Biaryls have been a persistent focus of interest for chemists since it was recognised, more than 80 years ago, that they can manifest the axial chirality that is inherent in structures consisting of intersecting dissymmetric planes. In recent decades their importance has risen steeply as this structural motif proved spectacularly successful in catalytic synthetic roles and was found to be significant in the context of biological activity. As a consequence, synthetic methods which allowed the construction of biaryls with axial stereocontrol have become highly desirable, and this article traces the development of non-resolution approaches to biaryls with a chosen axial configuration.

Journal Article↗

Functionalized cyclobutenes via multicomponent thermal [2 + 2] cycloaddition reactions.

[reaction: see text] Enamine [2 + 2] cycloadditions can be achieved in useful yields simply by stirring a mixture of an aldehyde, diethylamine, a dialkyl fumarate, and potassium carbonate in acetonitrile at 25 degrees C, conditions that are compatible with the presence of a potential leaving group on the beta-position of the intermediate enamine. Methylation and elimination of the product cyclobutanes completes a mild nonphotochemical route to functionalized cyclobutenes.

Journal Article↗

Fine-tuning of biaryl dihedral angles: structural characterization of five homologous three-atom bridged biphenyls by X-ray crystallography.

The homologous series of three-atom bridged biaryls comprising 5,7-dihydro-1,2,3,9,10,11-hexamethoxydibenzo[c,e]oxepine, 6,7-dihydro-1,2,3,9,10,11-hexamethoxy-6-methyl-5H-dibenzo[c,e]azepinium chloride, 5,7-dihydro-1,2,3,9,10,11-hexamethoxydibenzo[c,e]thiepine, and the 6-oxide and 6,6-dioxide derivatives of the latter have been characterized by X-ray crystal structure analysis. Within this series the endocyclic and exocyclic biaryl dihedral angles vary over 10 degrees ranges, reflecting the changing balance of intramolecular (steric, geometric) and intermolecular (crystal packing) forces, the former being potential control elements for fine-tuning the helicity of the biaryl system.

Biphenyl Compounds↗