Stereochemistry and mechanism of electron impact induced elimination reactions in acenaphthenol and acetoxyacenaphthene

Abstract

The mechanisms for elimination of H2O from acenaphthenol and of AcOH from acetoxyacenaphthene under low energy conditions have been determined, using regiospecific and stereospecific deuterium labeling probes, and by measurement of ionization and appearance potentials for alternative pathways. Both concerted and stepwise processes must be invoked in order to explain the experimental data. Proximity effects appear to be the most important factors in determining mechanistic type.