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The importance of hydrogen bonding in the alkylation of phenols

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dc.contributor.author Alauddin, Mian Mohannad. en_US
dc.date.accessioned 2009-07-09T18:49:46Z
dc.date.available 2009-07-09T18:49:46Z
dc.date.issued 1982-07-09T18:49:46Z
dc.identifier.uri http://hdl.handle.net/10464/2158
dc.description.abstract Hydrogen bond assisted alkylation of phenols is compared with the classical base assisted reactions. The influence of solvents on the fluoride assisted reactions is discussed,· with emphasis on the localization of hydrogen bond charge density. Polar aprotic solvents such as DMF favour a-alkylation, and nonpolar aprotic solvents such as toluene favourC-alkylation of phenol. For more reactive and soluble fluorides, such as tetrabu~ylammoniumfluoride, the polar aprotic solvent favours a-alkylation and nonpolar aprotic solvent favours fluorination. Freeze-dried potassium fluoride is a better catalytic agent in hydrogen bond assisted alkylation reactions of phenol than the oven-dried fluoride. The presence of water in the alkylation reactions reduces the expected yield drastically. The tolerance of the reaction to water has also been studied. The use ofa phase transfer catalyst such as tetrabutylammonium bromide in the alkylation reactions of phenol in the presence of potassium fluoride is very effective under anhydrous conditions. Sterically hindered phenols such as 2,6-ditertiarybutyl-4-methyl phenol could not be alkylated even by using the more reactive fluorides, such as tetrabutylammonium fluoride in either polar or nonpolar aprotic solvents. Attempts were also made to alkylate phenols in the presence of triphenylphosphine oxide. en_US
dc.language.iso eng en_US
dc.publisher Brock University en_US
dc.subject Phenols. en_US
dc.subject Alkylation. en_US
dc.subject Hydrogen bonding. en_US
dc.title The importance of hydrogen bonding in the alkylation of phenols en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name M.Sc. Chemistry en_US
dc.degree.level Masters en_US
dc.contributor.department Department of Chemistry en_US
dc.degree.discipline Faculty of Mathematics and Science en_US


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