851636-93-6Relevant articles and documents
Facile C-N cleavage in a series of bridged lactams
Lei, Yao,Wrobleski, Aaron D.,Golden, Jennifer E.,Powell, Douglas R.,Aube, Jeffrey
, p. 4552 - 4553 (2005)
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