CYCLIC QUATERNARY AMMONIUM SALTS FROM HALOGENATED ALIPHATIC TERTIARY AMINES

1930 ◽  
Vol 52 (1) ◽  
pp. 287-294 ◽  
Author(s):  
E. R. Littmann ◽  
C. S. Marvel
Keyword(s):  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Tertiary Amines

Strategies for the Synthesis of N-Arylammonium Salts

Synthesis ◽  
2017 ◽  
Vol 49 (16) ◽  
pp. 3535-3545 ◽  
Author(s):  
Charles Diesendruck ◽  
Shlomy Arava
Keyword(s):  
Organic Chemistry ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Tertiary Amines ◽  
Pyrylium Salts ◽  
Menshutkin Reaction ◽  
Nucleophilic Aromatic Substitutions ◽  
Ammonium Compounds ◽  
General Method

The N-arylation of tertiary amines to provide sp3 quaternary ammonium salts is a challenge in organic chemistry. To date, no general method for such arylations has been established. Here, we summarize a variety of strategies that have been tested, starting with harsh nucleophilic aromatic substitutions, through to the use of copper catalysis and the application of strong electrophiles, such as phenyl cations and benzynes. The achievements and limitations of each method are summarized, and the challenges yet to be met in the synthesis of charged ammonium compounds are described.1 Introduction2 Alkylation of Anilines: The Menshutkin Reaction3 Arylations3.1 Nucleophilic Aromatic Substitutions by Tertiary Amines3.2 Preparation of N-Arylpyridinum Salts from Zincke and Pyrylium Salts3.3 Arylations Using Phenyl Cations3.4 Copper-Catalyzed Arylation of N-Heteroarenes3.5 Benzynes as Aryl Electrophiles4 Conclusions and Perspective

scholarly journals Synthesis and Surfactant Studies of Dialkyl Dimethyl Quaternary Ammonium Bromide Formulations

2006 ◽  
Vol 5 (3) ◽  
Author(s):  
Rocky Barney ◽  
Tony Stark ◽  
Dru Delaet
Keyword(s):  
Quaternary Ammonium ◽  
Carbon Chain ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Ammonium Bromide ◽  
Tertiary Amines ◽  
Alkyl Bromide ◽  
Component Systems ◽  
Multiple Component ◽  
Chain Lengths

Quaternary ammonium salts (otherwise known as quats) are commonly used active ingredients in biocide formulations used in the anti-microbial industry. Although quats have been established to be effective biocides, there are few studies investigating the maximization of biocidal efficacy in multiple component formulations using various carbon chain lengths. Reported here is the synthesis based on the Sn2 reaction of tertiary amines with alkyl bromide. Surfactant studies of the single and dual component systems were conducted, and the evaluation is explored.

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