Allylation of carboxylic acids under mild conditions

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dc.contributor.advisor Albiniak, Philip Anthony, 1977- Strayer, Timothy Allen 2014-12-16T16:12:53Z 2014-12-16T16:12:53Z 2014-12-13
dc.description en_US
dc.description.abstract 2-benzyloxy-1-methylpyridinium triflate (BnOPT) is a proven benzyl transfer reagent that is able to create benzyl esters from carboxylic acids that have been activated by a weak base. It is hypothesized that the method could be extended to transferring other resonance stabilized cations. Allyl transfer reagents based on the aforementioned benzyl transfer reagent are being investigated, namely 2-allyloxy-1-methylpyridinium triflate (AMPT) and 2-allyloxy-1- methyllepidinium triflate (AMLT). AMLT could give chemists another avenue of protection for carboxylic acids as allyl esters. These allyl groups are effective in the protection of carboxylic acids; they can withstand many possible transformations and they can be removed selectively by the use of a number of palladium-based catalysts. However, common pre-existing methods of installing allyl esters can be less selective or result in unwanted side reactions depending on what other functional groups are present on the substrate. Details of the development of the method and its efficacy on multiple substrates are presented in this thesis. en_US
dc.description.sponsorship Department of Chemistry
dc.description.tableofcontents Investigation of allyl esterification reactions -- Methodology and spectra.
dc.subject.lcsh Carboxylic acids
dc.subject.lcsh Esterification
dc.subject.lcsh Functional groups
dc.subject.lcsh Methanesulfonates
dc.title Allylation of carboxylic acids under mild conditions en_US
dc.title.alternative Title on signature form: Allylation of oxygen nucleophiles under mild conditions Thesis (M.S.) en_US

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  • Master's Theses [5293]
    Master's theses submitted to the Graduate School by Ball State University master's degree candidates in partial fulfillment of degree requirements.

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