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Menshutkin reaction

Chemical reaction

Menshutkin reaction

Chemical reaction

In organic chemistry, the Menshutkin reaction converts a tertiary amine into a quaternary ammonium salt by reaction with an alkyl halide. Similar reactions occur when tertiary phosphines are treated with alkyl halides.

Menshutkin-reaction

The reaction is the method of choice for the preparation of quaternary ammonium salts. Some phase transfer catalysts (PTC) can be prepared according to the Menshutkin reaction, for instance the synthesis of triethyl benzyl ammonium chloride (TEBA) from triethylamine and benzyl chloride:

Menshutkin reaction

Scope

Reactions are typically conducted in polar solvents such as alcohols. Even pyridines, which are considerably less nucleophilic than typical tertiary amines, react with dichloromethane at room temperature over a period of several days to weeks to give bis(pyridinium)methane salts.

In addition to solvent and alkylating agent, other factors strongly influence the reaction. In one particular macrocycle system the reaction rate is not only accelerated (150000 fold compared to quinuclidine) but the halide order is also changed

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History

The reaction is named after its discoverer, Nikolai Menshutkin, who described the procedure in 1890. Depending on the source, his name (and the reaction named after him) is spelled as Menšutkin, Menshutkin, or Menschutkin.

References

References

  1. W. R. Brasen. (1954). "o-Methylethylbenzyl Alcohol". Org. Synth..
  2. (16 January 1981). "N-alkylation of tertiary aliphatic amines by chloroform, dichloromethane and 1,2-dichloroethane". Journal of Chromatography A.
  3. ''Reaction of Dichlormethane with Pyridine Derivatives under Ambient Conditions'' Alexander B. Rudine, Michael G. Walter, and Carl C. Wamser [[J. Org. Chem.]] '''2010''', 75, 4292–95 {{doi. 10.1021/jo100276m
  4. ''Dramatic Acceleration of the Menschutkin Reaction and Distortion of Halide Leaving-Group Order'' Keith J. Stanger, Jung-Jae Lee, and Bradley D. Smith [[J. Org. Chem.]] '''2007''', 72, 9663–68 {{doi. 10.1021/jo702090p
  5. N. Menschutkin. Beiträgen zur Kenntnis der Affinitätskoeffizienten der Alkylhaloide und der organischen Amine ''Z. Physik. Chem.'' 5 ('''1890''') 589.
  6. N Menschutkin. Über die Affinitätskoeffizienten der Alkylhaloide und der Amine ''Z. Physik. Chem.'' 6 ('''1890''') 41.
  7. M B Smith, J March. ''March's Advanced Organic Chemistry'' (Wiley, 2001) ({{ISBN. 0-471-58589-0)
  8. ''Lexikon bedeutender Chemiker'' (VEB Bibliographisches Institut Leipzig, 1989) ({{ISBN. 3817110553
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