Reactions of Alkylbenzyldimethylammonium Halides with Amide in Liquid Ammonia

Carl L. Bumgardner, Hon Bin Hsu, F. Afghahi, William L. Roberts, Suzanne T. Purrington

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)2348-2353
Number of pages6
JournalJournal of Organic Chemistry
Issue number14
StatePublished - Feb 1 1979
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


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