In general, with the exception of fluorinated compounds, haloalkanes readily undergo nucleophilic substitution reactions or elimination reactions.
The reaction, formally a rearrangement, ranks under the elimination reactions as already observed by the original authors.
Methanesulfonates are used as intermediates in substitution reactions, elimination reactions, reductions, and rearrangement reactions.
Selenium in these reactions is almost always stereogenic, and the effect of epimerization at selenium (which is acid-catalyzed and occurs readily) on the elimination reaction is nearly unknown.
It was reasoned that a contaminant must have been present to cause this unexpected elimination reaction, and the cause was eventually determined to be traces of nickel salts.
This intermediate loses water in an elimination reaction to unsaturated carbonyl compound 4 and then loses water again in imine formation to quinoline 7.
Addition of alkali to the -substituted compound on the other hand leads to an elimination reaction with liberation of ethylene.
The carbanion proceeds in an elimination reaction to create the carboncarbon double bond.
