Journal of Organic Chemistry p. 3054 - 3059 (1985)
Update date:2022-08-11
Topics:
Lambert, Joseph B.
Boch, Richard J.
Larson, Eric G.
The Seyferth reagent has dual reactivity with electron-deficient alkenes. trans-1,2-Dichloroethene reacts both with the free carbene to give cyclopropane stereospecifically and with a complex between carbene and a second molecule of Seyferth reagent (homogeneous catalysis) to give a rearranged propene.The addition of other materials to the reaction mixture can have a profound effect on the ratio of the two pathways.Good ? donors such as p-xylene decrease the pathway to rearranged propene via the complexed carbene.Such materials thus serve as inhibitors to the process of homogeneous catalysis by forming a competing complex that does not go on to propene but instead reverts to free carbene.The existence of the inhibitor-carbene complex is supported by concentration studies.The presence of insoluble materials such as zinc chloride, on the other hand , serves to decrease the pathway that leads through free carbene to the cyclopropane.Free carbene may react with the surface of the additive and be removed as a reactive species.This latter process would have no effect on carbene previously complexed with the homogeneous catalyst, the Seyferth reagent , which could still proceed to rearranged propene.
View MoreNantong Advance Chemical Co., Ltd
Contact:86-13818730908
Address:Fine Chemical Industry Garden,Beixin Town,Qidong
Huangshi Shennong Chemical Technology Co., Ltd
Contact:+86-714-3072290
Address:Eastern industrial park , Tieshan district , Huangshi city ,Hubei province , China
Shanghai Sungo Technology Chemical Co., Ltd
Contact:0086-21-51385579
Address:Room2010, F/20, Tonghua Plaza, NO 345 Jinxiang Road, Jinqiao Export Processing Zone, Shanghai, 201206 P.R.CHINA
ChangZhou XiaQing Chemical Co., Ltd.
Contact:+86-519-88721665
Address:3# Hengluo Road, Henglin Town, Changzhou City, Jiangsu Province,China
Jiangsu Glory Chemical Co., Ltd.
Contact:+86-571-87896791
Address:Yanhua Chemical Park, Hongze, Huai'an, Jiangsu, China
Doi:10.1021/jo00821a049
(1971)Doi:10.3184/030823400103165617
(2000)Doi:10.1002/chem.201902845
(2019)Doi:10.1016/S0022-328X(00)98810-7
(1983)Doi:10.1007/s10600-017-2211-0
(2017)Doi:10.1021/acs.macromol.0c01697
(2020)