Journal of Organic Chemistry p. 5946 - 5953 (1995)
Update date:2022-08-05
Topics:
Barrett, Dawn M. Y.
Kahwa, Ishenkumba A.
Mague, Joel T.
McPherson, Gary L.
Protection of NH2 groups as phthalimides using a mixture of acetic acid, phthalic anhydride,and the relevant polyamine can take unusual routes.For diethylenetriamine the major product is diphthalimidodiethylammonium-hydrogen phthalate (DPDAH-HP).For triethylenetetraamine, ethylene migration products N,N-bis(2-phthalimidoethyl)piperazine (2) and N,N',N''-(nitrilotriethylene)trisphthalimide (3) were obtained from room temperature and refluxing reaction mixtures, respectively.The crystal structures of 2, 3, and DPDAH-HP were determined and reveal a series of stabilizing complementary interactions for these favored products (i.e., offset ?-? stacking and C-H...O and possibly C-H...N hydrogen bonds (2), electrostatic interactions between the amine and pyrrolic functionalities (3), and offset ?-? stacking and N-H...O hydrogen bonding (DPDAH-HP).The DPDAH-HP units stack along a screw axis parallel to the b-direction to yield a striking
Jiangsu Wanlong Chemical Co., Ltd.
website:http://www.wanlongchem.com
Contact:+86-511-86810993 0086-511-8681 0888;
Address:Quanzhou Town, Danyang City, Jiangsu
Contact:86-511-85210668 0511-85210668, 85210818, 85210898
Address:Yihai Garden E-902,NO.99 Daxi RD., Zhenjiang Jiiangsu ,China
Nanjing Norris Pharm Technology Co., Ltd.
Contact:+86-13901585132
Address:2 Qiande Road, Jiangning sciencepark Hi-Tech Zone, Nanjing, P.R.China
Nanjing Chemzam Pharmtech Co., Ltd.
Contact:+86-25-86462165,+86-13915979898
Address:C5-1,6 Maiyue Road,Maigaoqiao,Nanjing,Jiangsu,China
Zhejiang Sanmei Chemical Industry Co., Ltd
Contact:86-579-87633213
Address:Huchu Industrial Zone, Qingnian Rd., Wuyi County, Zhejiang Prov., China.
Doi:10.1039/c39840000418
(1984)Doi:10.1021/acs.oprd.0c00216
(2020)Doi:10.1016/S0957-4166(98)00045-7
(1998)Doi:10.1021/jo981322c
(1998)Doi:10.1016/S0957-4166(98)00025-1
(1998)Doi:10.1039/a708374b
(1998)