Show simple item record

dc.contributor.advisorReinecke, Manfred G.
dc.contributor.authorGrins, Georgeen_US
dc.description.abstractHeating pyridines with Raney nickel and 1-decanol resulted in methylation at the free alpha positions. [Diagram] Similarly, 3-picoline gave 2,5-lutidine, 4-picoline gave 2,4-lutidine and 2,4,6-collidine, 4-methoxypyridine gave 2-methyl-4-methoxypyridine, quinoline gave 2-methylquinoline and 8-methylquinoline, phenol gave o-cresol, and benzoquinuclidine gave 8-methylbenzoquinuclidine. The specificity of this unusual methylation reaction makes it unique from the normal aromatic substitution reactions of pyridine. The mechanism is postulated to involve dehydroxymethylation of 1-decanol to produce nonane and a one-carbon fragment (believed to be similar to methylene) adsorbed on the catalyst. The specificity of the reaction indicates that pyridine is adsorbed on the catalyst via the nitrogen lone-pair electrons thus making the alpha-carbons available to attack by the one-carbon fragment adsorbed on the Raney nickel. The methylation of phenol and benzoquinuclidine, although in low yield, showed that lone-pair electrons other than those of pyridine can act to anchor a molecule to the catalyst and allow methylation.
dc.format.extentx, 193 leaves, bound : illustrationsen_US
dc.format.mediumFormat: Printen_US
dc.relation.ispartofTexas Christian University dissertationen_US
dc.titleThe catalytic alpha-methylation of pyridinesen_US
dc.typeTexten_US of Chemistry
local.collegeCollege of Science and Engineering
local.departmentChemistry and Biochemistry
local.academicunitDepartment of Chemistry
local.subjectareaChemistry and Biochemistry
dc.identifier.callnumberMain Stacks: AS38 .G75 (Regular Loan)
dc.identifier.callnumberSpecial Collections: AS38 .G75 (Non-Circulating) of Philosophy Christian University

Files in this item


There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record