Lei Yao, Wrobleski Aaron D, Golden Jennifer E, Powell Douglas R, Aubé Jeffrey
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Room 4070, Malott Hall, University of Kansas, Lawrence, KS 66045-7582, USA.
J Am Chem Soc. 2005 Apr 6;127(13):4552-3. doi: 10.1021/ja050214m.
A series of strained bi- and tricyclic amides has been shown to be unusually sensitive to cleavage of the C-N bond adjacent to the amide moiety. This bond undergoes facile breaking when subjected to treatment with H2/Pd(OH)2, MeI, and DDQ. In each case, the reaction is highly regioselective and mainly results in breaking the C-N bond that deviates the farthest from its natural planar state. Preliminary experiments that bear on the mechanisms of these reactions are described.
一系列的张力双环和三环酰胺已被证明对酰胺部分相邻的C-N键的断裂异常敏感。当用H2/Pd(OH)2、MeI和DDQ处理时，该键容易断裂。在每种情况下，反应都具有高度的区域选择性，主要导致偏离其天然平面状态最远的C-N键断裂。描述了与这些反应机制相关的初步实验。
