Journal of Organic Chemistry p. 3499 - 3508 (1995)
Update date:2022-09-26
Topics:
Whitaker, Craig M.
Kott, Kevin L.
McMahon, Robert J.
We described the preparation and characterization of several new arylphosphine oxides, which are of interest as second-order nonlinear optical materials. (4-Aminophenyl)diphenylphosphine oxide (1a), bis(4-aminophenyl)phenylphosphine oxide (2a), and (4-aminophenyl)bis<4'-(trifluoromethyl)phenyl>phosphine oxide (5) were prepared by addition of aryl Grignard and organolithium reagents containing protected amines to phosphorus oxyhalides.Alternatively, 1a was prepared by treatment of (4-bromophenyl)diphenylphosphine oxide with azidomethyl phenyl sulfide, followed by hydrolysis. (4-Aminophenyl)(4'-nitrophenyl)phenylphosphine oxide (6) was prepared by nucleophilic aromatic substitution of bis(4-fluorophenyl)phenylphosphine oxide to give the corresponding dinitro compound, followed by selective mono-reduction.The X-ray crystal structure of (4-aminophenyl)diphenylphosphine oxide (1a), along with those of mono-, di-, and trihydroxy triphenylphosphine oxides 1b, 2b, and 3b, exhibit extensive intermolecular hydrogen bonding.The hydrogen bonding in 1a and 1b produces chains of arylphosphine oxide molecules with a head-to-tail alignment; the chains pack in an antiparallel manner to produce solid-state structures that display only slight deviations from centrosymmetry.
View MoreContact:+86-21-38122007
Address:2, Lane 1123, Kangqiao Road, Pudong New Area, Shanghai
Xiamen Hisunny Chemical Co.,Ltd
website:http://www.hisunnychem.com
Contact:+86-592-3327115
Address:Unit 603,No.879,Xiahe Road,Meixin Building,Xiamen,China
Contact:+86 21 34123252
Address:14, 4580 Dushi, Shanghai, China
VanderArk International Limited
Contact:86-10-82437576
Address:Qing He
website:http://www.chinabarton.com
Contact:+86-573-82719618
Address:No. 162 Fumin Road, Honghe Town,
Doi:10.1021/jo010043d
(2001)Doi:10.1039/a801269e
(1998)Doi:10.1021/jo01209a011
(1940)Doi:10.1016/S0277-5387(00)00605-7
(2001)Doi:10.1271/bbb.65.305
(2001)Doi:10.1016/S0957-4166(01)00023-4
(2001)