The bent bond / antiperiplanar hypothesis and the thermal rearrangement of cyclopropyl halides and tosylates The mechanism of solvolysis of cyclopropyl halides and tosylates yielding allylic products is deduced at the molecular level through the […]
Introduction to biocomputing in the pharmaceutical industry. Topics include molecular modeling, rational drug design, high throughput screening and combinatorial chemistry, protein modeling and 3D bioinformatics. Course includes lectures and a computer laboratory component. Due to […]
Due to ongoing COVID-19 restrictions, the Winter 2022 edition of CHEM 2422 “Introductory Organic Chemistry: Reactivity” will be taught by alternate delivery methods until further notice.Course Syllabus
The Bent Bond / Antiperiplanar Hypothesis and the Chemical Reactivity of Annulenes. The properties and stereochemical reactivity of cyclobutadiene, benzene, cyclooctatetraene and the [10]- to [14]annulenes can be uniformly rationalized through the bent bond /antiperiplanar […]
Bent Bond/Antiperiplanar Hypothesis: Modulating the Reactivity and the Selectivity in the Glycosylation of Bicyclic Pyranoside Models Glycosylation reactions were performed on a series of bicyclic C2-substituted pyranoside models to isolate and analyze factors that control […]
Applying the bent bond / antiperiplanar hypothesis to the stereoselective glycosylation of bicyclic furanosides The glycosylation stereoselectivities for a series of bicyclic furanoside models have been carried out in the presence of weak nucleophiles. These […]
The Bent Bond/Antiperiplanar Hypothesis (aka BBAH) is a conceptually novel orbital model for rationalizing the conformation and stereochemical reactivity of organic molecules containing various types of unsaturation. The BBAH is based on the Slater-Pauling bent […]
Thermal Rearrangement of Optically Active Tetradeuterated-2-methoxymethyl-methylenecyclopropane and the Bent Bond/Antiperiplanar Hypothesis The thermolysis of an optically active tetradeuterated 2-methoxymethyl methylenecyclopropane produces a specific ratio of eight possible rearrangement stereoisomers. Despite numerous efforts, this reaction and […]
Bent Bonds and the Antiperiplanar Hypothesis. A Model to Account for Sigmatropic [1,n]-Hydrogen Shifts Sigmatropic hydrogen shifts are rationalized using the BBAH involving antiperiplanar displacement of radical intermediates. The stereochemistry of both thermal and photochemical […]
High Temperature Isomerization of Benzenoid Polycyclic Aromatic Hydrocarbons. An Analysis through the Bent Bond and Antiperiplanar Hypothesis Orbital Model. The properties and stereochemical reactivity of cyclobutadiene, benzene, cyclooctatetraene and the [10]- to [14]annulenes can be […]
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