World Library  
Flag as Inappropriate
Email this Article

Sommelet–Hauser rearrangement

Article Id: WHEBN0025092685
Reproduction Date:

Title: Sommelet–Hauser rearrangement  
Author: World Heritage Encyclopedia
Language: English
Subject: Quaternary ammonium cation, 2,3-sigmatropic rearrangement, Stevens rearrangement
Collection:
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Sommelet–Hauser rearrangement

The Sommelet–Hauser rearrangement (named after M. Sommelet[1] and Charles R. Hauser[2]) is a rearrangement reaction of certain benzyl quaternary ammonium salts.[3][4] The reagent is sodium amide or another alkali metal amide and the reaction product a N-dialkyl benzyl amine with a new alkyl group in the aromatic ortho position.

Mechanism

The benzylic methylene proton is acidic and deprotonation takes place to the ylide. The second step is a 2,3-sigmatropic rearrangement.

The Stevens rearrangement is a competing reaction.

References

This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 


Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.