Conformational communication between the Ar-CO and Ar-N axes in 2,2′-disubstituted benzanilides and their derivatives

被引:27
作者
Clayden, Jonathan [1 ]
Vallverdu, Lluis [1 ]
Helliwell, Madeleine [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
关键词
D O I
10.1039/b602912d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzanilides containing two or more potentially stereogenic amide axes exist in solution as mixtures of conformers which are detectable by NMR. For simple tertiary benzanilides carrying an ortho substituent on each ring, conformational control can be high ( up to about 10 : 1) providing the substituents are large, indicating that the two axes are in conformational communication with one another. For more complex diamides, conformational communication breaks down, and mixtures of conformers are evident by NMR.
引用
收藏
页码:2106 / 2118
页数:13
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