The Journal of Organic Chemistry

The tertiary amide as an effective director of ortho lithiation

P Beak, RA Brown

文献索引：Beak, Peter; Brown, Roger A. Journal of Organic Chemistry, 1982 , vol. 47, # 1 p. 34 - 46

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被引用次数: 238

摘要

The tertiary amides NJV-diethylbenzamide (1) and NJV-diisopropylbenzamide (3) give the ortho-lithiated species 2 on treatment with sec-BuLiITMEDA or n-BuLilTMEDA, respectively, at-78" C. Lithiation of 1 followed by reaction with either methyl iodide, ethyl iodide, benzophenone, acetone, benzaldehyde, or trimethoxyborane-hydrogen peroxide gives the expected ortho substituted product. Intramolecular competition between the diethylamido ...