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The Base-Promoted Rearrangements of Quaternary Ammonium Salts

  1. Stanley H. Pine

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or018.04

Organic Reactions

Organic Reactions

How to Cite

Pine, S. H. 2011. The Base-Promoted Rearrangements of Quaternary Ammonium Salts. Organic Reactions. 18:4:403–464.

Author Information

  1. California State College, Los Angeles, California

  1. I thank the College for a creative research leave in the spring quarter, 1969, during which the major portion of this manuscript was written. I also thank Janice L. Romstad, du Pont Experimental Station, for assistance in searching the chemical literature.

Publication History

  1. Published Online: 15 MAR 2011

Abstract

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