Menschutkin Reaction

N. Menschutkin, Z. Physik. Chem. 5, 589 (1890); 6, 41 (1890).

Reaction of tertiary amines with alkyl halides to form quaternary salts:



Mechanistic studies: C. K. Ingold, Structure and Mechanism in Organic Chemistry (Cornell Univ. Press, New York, 2nd ed., 1969) p 435; M. H. Abraham, Progr. Phys. Org. Chem. 11, 1 (1974); E. M. Arnett, R. Reich, J. Am. Chem. Soc. 102, 5892 (1980); S. Shaik et al., ibid. 116, 262 (1994); S. H. Kim et al., J. Phys. Org. Chem. 11, 254 (1998). Solvent effects: J.-L. M. Abboud et al., J. Phys. Chem. 93, 214 (1989); S.-G. Kang et al., Bull. Chem. Soc. Japan. 66, 972 (1993).