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dc.contributor.advisorOtsuki, Testuo
dc.contributor.authorIverson, Cameron
dc.date.accessioned2020-08-13T14:56:01Z
dc.date.available2020-08-13T14:56:01Z
dc.date.issued2003-01-01 0:00
dc.identifier.urihttps://scholar.oxy.edu/handle/20.500.12711/723
dc.description.abstractDerivatives of 1,4-naphthoquinone are utilized as anti-fungal, antibacterial, and potential anticancer pharmaceuticals, which often show unexpected reactivities. Here we study the reactivity of 2-bromo-3-methyl-1,4-naphthoquinone toward primary and secondary amines. In the reaction with primary amines in methanol, contrary to our expectations, demethylation of 2-bromo-3-methyl-1,4-naphthoquinone generates 2-alkylamino-3-bromo-1,4-naphthoquinone as the major product. Furthermore, secondary amines such as N-ethylmethylamine gave 2-methylamino-3-bromo-1,4-naphthoquinone, presumably as the secondary reaction product. Unexpectedly, the reaction of 2-bromo-3-ethyl-1,4-naphthoquinone with primary, secondary, and tertiary amines yields very different results. In the reaction 2-bromo-3-ethyl-1,4-naphthoquinone with propylamine, for example, substitution occurs for the bromine. We believe this is due to the varying acidity between the two 2-alkyl-3-bromo-1,4-naphthoquinones. The scope and limitations of the reaction and reaction mechanism are studied.
dc.description.sponsorshipSupport provided by:Norris Fellowship
dc.titleReaction of 2-alkyl-3-bromo-1,4-Naphthoquinone with Amines; A Novel Demethylation Reaction.
dc.typearticle
dc.abstract.formathtml
dc.description.departmentchem
dc.source.issueurc_student
dc.source.issueurc_student
dc.identifier.legacyhttps://scholar.oxy.edu/urc_student/1136
dc.source.statuspublished


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