Acidity measurements on pyridines in tetrahydrofuran using lithiated silylamines

RR Fraser, TS Mansour, S Savard

文献索引：Fraser, Robert R.; Mansour, Tarek S.; Savard, Sylvain Journal of Organic Chemistry, 1985 , vol. 50, # 17 p. 3232 - 3234

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被引用次数: 148

摘要

The variation in the acidity of a methyl group as a function of its position on the pyridine ring is substantial. While the weaker acidity of 3-picoline is expected on the basis of its relative inertness to base-catalyzed condensations' it is surprising that 4-picoline is significantly more acidic than the 2-isomer. The difference could be the result of a repulsive dipolar interaction between the lithiomethyl group and the lone pair on nitrogen or may simply ...