TY - JOUR
T1 - Toward poly(aminophthalimide), structures of dimers and trimers
AU - Katayama, H.
AU - Greef, de, T.F.A.
AU - Kooijman, H.
AU - Spek, A.L.
AU - Vekemans, J.A.J.M.
AU - Meijer, E.W.
PY - 2007
Y1 - 2007
N2 - Poly(aminophthalimide) (PAP) dimers and trimers have been synthesized by palladium-catalyzed cross-coupling reactions of 3-aminophthalimides with 3-chloro- and 3,6-dichlorophthalimide, respectively. When Pd(OAc)2, XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), and K3PO4 are used, the C–N bond-forming reactions proceed quantitatively. The structures of those oligomers are examined by experimental and theoretical techniques including NMR, IR, single-crystal X-ray diffraction, and DFT calculations. The strong preference for cisoid structure of the diphthalimidylamine unit bearing a bifurcate hydrogen bonding is disclosed. Therefore, the aminophthalimide backbone is a highly promising candidate for the construction of a dynamically ordered helical structure.
AB - Poly(aminophthalimide) (PAP) dimers and trimers have been synthesized by palladium-catalyzed cross-coupling reactions of 3-aminophthalimides with 3-chloro- and 3,6-dichlorophthalimide, respectively. When Pd(OAc)2, XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), and K3PO4 are used, the C–N bond-forming reactions proceed quantitatively. The structures of those oligomers are examined by experimental and theoretical techniques including NMR, IR, single-crystal X-ray diffraction, and DFT calculations. The strong preference for cisoid structure of the diphthalimidylamine unit bearing a bifurcate hydrogen bonding is disclosed. Therefore, the aminophthalimide backbone is a highly promising candidate for the construction of a dynamically ordered helical structure.
U2 - 10.1016/j.tet.2007.04.002
DO - 10.1016/j.tet.2007.04.002
M3 - Article
VL - 63
SP - 6642
EP - 6653
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 28
ER -