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No 4-phenylpyridine is formed in the reaction of phenyllithium with pyridine. When phenyllithium reacts with a 3-alkylpyridine the main product is the 3-alkyl-2-phenylpyridine if the alkyl group is methyl, ethyl, or isopropyl, but it is the 5-alkyl-2-phenylpyridine when the substituent is t-butyl. Methods are described for the separation and quantitative analysis of mixtures of 3-alkyl- and 5-alkyl-2-phenylpyridines using vapor phase chromatography. The results are discussed briefly and possible explanations of the observed orientations are mentioned.
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Abramovitch et al. (1962) studied this question.
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