Facile C-N cleavage in a series of bridged lactams
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. Copyright
Lei, Yao,Wrobleski, Aaron D.,Golden, Jennifer E.,Powell, Douglas R.,Aube, Jeffrey