Competitive elimination and rearrangement reactions of alkylbenzyldimethylammonium ions with amide ion in liquid ammonia have been investigated. Elimination is largely dependent on the geometry of the alkyl group. Cyclohexyl-and tert-butylbenzyldimethylammonium halides undergo more Stevens than Sommelet-Hauser rearrangement with amide ion in liquid ammonia. The results are interpreted in light of the reactivity of the intermediate ylide. The structure of the rearrangement product from isopropylbenzyldimethylammonium iodide has been reassigned.
ASJC Scopus subject areas
- Organic Chemistry