Physical Sciences and Mathematics Commons^™

Trimethylsulfonium Methanesulfonate, Frank R. Fronczek, Rolanda J. Johnson, Robert M. Strongin

Chemistry Faculty Publications and Presentations

In the title compound, C₃H₉S⁺.CH₃O₃S^-, a thermal decomposition product of dimethyl sulfoxide, both cation and anion lie on mirror planes. In the cation, the S atom lies 0.792 (2) Å out of the plane defined by the three C atoms, with S-C distances of 1.781 (2) and 1.786 (3) Å. In the anion, the S-O distances are 1.4556 (14) and 1.4646 (19) Å, and the S-C distance is 1.759 (3) Å.

Cerumen Composition By Flash Pyrolysis-Gas Chromatography/Mass Spectrometry, Craig N. Burkhart, Michael A. Kruge, Craig G. Burkhart, Curtis Black

Department of Earth and Environmental Studies Faculty Scholarship and Creative Works

Objective: To assess the chemical composition of cerumen by flash pyrolysis-gas chromatography/mass spectrometry.

Study Design: Collected earwax specimens were fractionated into residue and supernatant by means of deoxycholate. This natural bile acid produces significantly better disintegration of earwax in vitro than do presently available ceruminolytic preparations, and also has demonstrated excellent clinical results in vivo to date.

Patients: The sample for analysis was obtained from a patient with clinical earwax impaction.

Results: The supernatant is composed of simple aromatic hydrocarbons, C₅-C_{l 7} straight-chain hydrocarbons, a complex mixture of compounds tentatively identified as diterpenoids, …

Meso-1, 2-Bis (Methylazo)-1, 2-Diphenylethane, Craig A. Bayse, Barry K. Carpenter, Rudy L. Luck

Chemistry & Biochemistry Faculty Publications

The title compound, meso-1,2-bis(methyldiazenyl)-1,2-diphenylethane, C16H18N4, is arranged in a disordered manner around an inversion point. The N—N atom distances in the azo group of 1.192 (8) and 1.195 (8) Å, and the C—C atom distances in the ethylene moiety at 1.512 (8) and 1.503 (8) Å in the two models [refined to 51.7 (6) and 48.3 (6)% occupancies] were not significantly different.

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

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.

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

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

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.