Isotope effect studies on elimination reactions. VII. The stereochemistry of elimination from 2-phenylethylammonium ions

The stereochemistry of the base-promoted elimination reactions of 2-phenylethyltrimethylammonium and 2-phenylethyldimethylanilinium ions has been investigated using both ethoxide ion in ethanol and t-butoxide in t-butyl alcohol as base-solvent systems. The proton magnetic resonance spectroscopic analysis of the deuterated styrene products formed from the reactions of the threo-2-phenylethylammonium-1,2-d2 ions established that elimination proceeds more than 95% by an anti process.