Issue 18, 1976

Organometallic compounds of group II. Part VII. Preparation of 4-alkylpyridines by reactions of some light metals with alkyl halides in pyridine

Abstract

Ether-free alkylmagnesium halides and alkyl-lithium compounds react with pyridine in the absence of the free metals to form 2-alkylpyridines; but in the presence of the free metals, 4-alkylpyridines are also formed. The reaction of an alkyl halide with the metal in situ in pyridine gives the 4-alkylpyridine essentially free from the 2-isomer. The use of alkyl chlorides and magnesium provides the best combination. Allyl chloride reacts with magnesium in pyridine to give 4-n-propylpyridine. The reactions of n-butyl chloride and magnesium in 2-picoline, 4-picoline, and collidine give a mixture of 2-n-pentylpyridine and 4-n-butyl-2-methylpyridine, 4-n-pentylpyridine, and a mixture of ‘bicollidinyls,’ respectively. It is suggested that the key step in the new 4-alkylation reaction involves abstraction of an alkylmetallic species by an intermediate derived from pyridine by electron transfer from the free metal.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1976, 1977-1983

Organometallic compounds of group II. Part VII. Preparation of 4-alkylpyridines by reactions of some light metals with alkyl halides in pyridine

D. Bryce-Smith, P. J. Morris and B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1, 1976, 1977 DOI: 10.1039/P19760001977

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