The Base-Promoted Rearrangements of Quaternary Ammonium Salts
Published Online: 15 MAR 2011
Copyright © 2004 by Organic Reactions, Inc. Published by John Wiley & Sons, Inc.
How to Cite
Pine, S. H. 2011. The Base-Promoted Rearrangements of Quaternary Ammonium Salts. Organic Reactions. 403–464.
- Published Online: 15 MAR 2011
The based-promoted rearrangements of quaternary ammonium salts can be divided into two categories. In the Stevens rearrangement one-alkyl group migrates from the quaternary nitrogen group to the alpha carbon atom of a second alkyl group. The Somelet-Hayser rearrangement involves migration to the ortho position of a benzyl quaternary ammonium salt. When structurally feasible, both rearrangements may occur simultaneously although experimental conditions markedly affect the competing pathways.
Keywords: Sommelet-Hauser rearrangements; Stevens rearrangements; quaternary ammonium salts; competitive rearrangements. experimental conditions