Chemistry and Materials Science Seminar: Acetal substitution reactions involving oxocarbenium ions
Chemistry and Materials Science Seminar
Acetal substitution reactions involving oxocarbenium ions: conformational analysis, stereoelectronic effects, and reactivity determine stereoselectivity
Dr. Keith Woerpel
Professor of Medicinal Chemistry
NYU
Abstract:
Oxocarbenium ions, which are reactive intermediates in many acetal substitution reactions, adopt conformations that cannot be explained by consideration of steric effects. In cyclic oxocarbenium ions, axially substituted conformers are generally favored because of stabilizing electrostatic forces between the partially negatively charged substituents and the cationic carbon atom. Proximal and distal electron-donating and electron-withdrawing groups can affect the structures and reactivities of oxocarbenium ions.
Intended Audience:
Undergraduates, graduates, experts. Those with interest in the topic.
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