Journal of Organometallic Chemistry p. 1892 - 1897 (2007)
Update date:2022-08-03
Topics:
Varaprath, Sudarsanan
Stutts, Debra H.
The potential of trichloroisocyanuric acid (TCCA) as a chlorination agent for efficient conversion of Si-H functional silanes and siloxanes to the corresponding Si-Cl functional moieties was explored. In comparison to methods using other chlorinating agents, TCCA is inexpensive, results in a much faster reaction and produces a high purity product with a conversion that is essentially quantitative. A variety of chloro derivatives of linear and cyclic structures have been synthesized from silicon hydrides using this reagent with impressive yields that typically exceed 90%: PhSiCl3 (97.5%); PhMeSiCl2 (95.5%); Ph3SiCl (97.5%); Vi3SiCl (98.7%); (EtO)3SiCl (99.7%); t-Bu3SiCl (~100%); (MeClSiO)4 (86.5%); (MeClSiO)5 (95%); (MeClSiO)7 (96.5%); Ph(OEt)2SiCl (98%); ClMe2SiOSiMe2Cl (98.6%); ClMe2SiOSiMeClOSiMe2Cl (94.6%); ClMe2Si(OSiMeCl)2OSiMe2C l (92.3%); (Me3SiO)3SiCl (97%); Me3SiOSiClPhOSiMe3 (99%); Me3SiO(SiMeClO)3SiMe3 (95.7%); ClSi(OSiMe3)2OSi(OSiMe3) 2Cl (93.6%). For monohydridosilanes, dichloromethane (CH2Cl2) was a suitable solvent in which nearly quantitative conversion was observed within several minutes following the addition of the silanes to TCCA. For certain cyclic and linear siloxanes, and especially silanes containing multiple hydrogen atoms on the same silicon for which the reaction is sluggish in CH2Cl2, tetrahydrofuran (THF) was the preferred solvent. For a sterically demanding silane that did not undergo chlorination even in THF viz., HSi(OSiMe3)2O-Si(OSiMe3)2H, 1,2-dichloroethane was the best solvent.
View MoreEvergreen Chemical Industry Ltd.
Contact:86-553-4918210
Address:6#2-602 Wanhaobailing
Contact:86-551-63540590
Address:No 1388 Furong Rd., Hefei, Anhui, China
Jiangsu Willing Bio-Tech Co ltd
website:http://www.willingbio.com/
Contact:+86 18796909136
Address:No 18 Guoqiao Road
website:http://www.chemdow.com
Contact:0086-10-82435335
Address:Room 401,Unit 3,4th Floor,Shangdijiayuan,Shangdi East Road, Haidian District,Beijing
Shanghai Forever Biotech Co., Ltd.
Contact:+86-21-69734790
Address:Room 5017/5019、5022、5024 of Technology Innovation Centre, No.1155, Gongyuan East Rd, QingPu District, Shanghai China.
Doi:10.1002/hlca.19690520617
(1969)Doi:10.1039/jr9650000782
(1965)Doi:10.1021/acs.orglett.9b00538
(2019)Doi:10.1021/om034126r
(2003)Doi:10.3184/174751913X13668131126257
(2013)Doi:10.1016/0032-3950(69)90314-1
(1969)