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Full-Text Articles in Physical Sciences and Mathematics
Lewis Acid Catalyzed Reactions Of Aziridino-Olefins, Steven Tymonko '01
Lewis Acid Catalyzed Reactions Of Aziridino-Olefins, Steven Tymonko '01
Honors Projects
Electrophilic reactions resulting in the formation of new carbon-carbon bonds are important tools in organic synthesis. For example, the acid catalyzed cyclization of epoxy olefins has been well documented, while similar cyclizations with aziridines have been largely unexplored. The aim of this project is to develop and demonstrate the formation of a carbocyclic compound from aziridino-olefins utilizing a Lewis acid to catalyze the cyclization. In working toward this goal, a number of aziridino-olefins were synthesized from isoprenoid start materials. These aziridino-olefins were then reacted with both Lewis and protic acids in an attempt to induce cyclization. As a result, we …
An Efficient Method For The Chemoselective Synthesis Of Acylals From Aromatic Aldehydes Using Bismuth Triflate, Ram Mohan, Marc Carrigan, Kyle Eash, Matthew Oswald
An Efficient Method For The Chemoselective Synthesis Of Acylals From Aromatic Aldehydes Using Bismuth Triflate, Ram Mohan, Marc Carrigan, Kyle Eash, Matthew Oswald
Scholarship
Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 0.10 mol% Bi(OTf)3•xH2O. Ketones are not affected under the reaction conditions. The highly catalytic nature of bismuth triflate and the fact that it is relatively non-toxic, easy to handle and insensitive to small amounts of air and moisture makes this procedure especially attractive for large-scale synthesis.
The Discovery-Oriented Approach To Organic Chemistry. 4. Epoxidation Of P-Methoxy-Trans-Β-Methylstyrene. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Rebecca Centko
The Discovery-Oriented Approach To Organic Chemistry. 4. Epoxidation Of P-Methoxy-Trans-Β-Methylstyrene. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Rebecca Centko
Scholarship
Epoxidation of alkenes using peroxyacids is one of the most fundamental reactions in organic chemistry, yet there are very few examples of laboratory experiments that illustrate this important reaction. We have developed a discovery-oriented lab experiment that illustrates epoxidation of alkenes as well as the reactivity of epoxides toward acids. The experiment involves reaction of p-methoxy-trans-β-methylstyrene (trans-anethole) with m-chloroperoxybenzoic acid (MCPBA), in both the absence and presence of a buffer, followed by product identification using 1H NMR, 13C NMR, and IR spectroscopy. The added element of discovery ensures that students' interest and enthusiasm are retained.
Deprotection Of Ketoximes Using Bismuth(Iii) Nitrate Pentahydrate, Ram Mohan, Bryce Nattier, Kyle Eash
Deprotection Of Ketoximes Using Bismuth(Iii) Nitrate Pentahydrate, Ram Mohan, Bryce Nattier, Kyle Eash
Scholarship
Ketoximes undergo facile deprotection in acetone-H20 (9: 1) in the presence 01' 0.5 equivalents of Bi(N03h•5H20. Bismuth(III) nitrate is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the use of a relatively nontoxic solvent system make this method an attractive alternative to existing routes for deprotection of ketoximes.
A Facile And Efficient Method For The Rearrangement Of Aryl-Substituted Epoxides To Aldehydes And Ketones Using Bismuth Triflate, Ram Mohan, Kaushik Bhatia, Kyle Eash, Nicholas Leonard, Matthew Oswald
A Facile And Efficient Method For The Rearrangement Of Aryl-Substituted Epoxides To Aldehydes And Ketones Using Bismuth Triflate, Ram Mohan, Kaushik Bhatia, Kyle Eash, Nicholas Leonard, Matthew Oswald
Scholarship
Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01–0.1 mol% Bi(OTf)3•xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C―O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3•Et2O, currently used to effect epoxide rearrangements.
The Discovery-Oriented Approach To Organic Chemistry. 5. Stereochemistry Of E2 Elimination: Elimination Of Cis- And Trans-2-Methylcyclohexyl Tosylate, Ram Mohan, Marcus Cabay, Brad Ettlie, Adam Tuite, Kurt Welday
The Discovery-Oriented Approach To Organic Chemistry. 5. Stereochemistry Of E2 Elimination: Elimination Of Cis- And Trans-2-Methylcyclohexyl Tosylate, Ram Mohan, Marcus Cabay, Brad Ettlie, Adam Tuite, Kurt Welday
Scholarship
The E2 elimination is one of the most important reactions in organic chemistry and is discussed in considerable detail in a sophomore organic course. We have developed a discovery-oriented lab that illustrates the stereochemistry of the E2 elimination reaction and is a good exercise in 1H NMR spectroscopy. The added element of discovery insures that student interest and enthusiasm are retained.