Journal of the Chemical Society. Perkin transactions I p. 1971 - 1977 (1996)
Update date:2022-07-29
Topics:
Matano, Yoshihiro
Yoshimune, Masanori
Azuma, Nagao
Suzuki, Hitomi
Treatment of triphenylbismuth difluoride with alkenyltrimethylsilanes 1 or trimethylsilyl cyanidealkenyltrialkylstannanes 3 in the presence of boron trifluoride-diethyl ether gave the corresponding alkenyltriphenylbismuthonium tetrafluoroborates 2 in moderate to good yields. An X-ray crystallographic analysis of the salt 2e confirmed the distorted tetrahedral geometry of the central bismuth atom. When treated with a sulfinate 5 or the thiolate 11, the salts 2 readily transferred both the vinyl and phenyl moieties to these nucleophiles to afford the sulfones 7-10 or the sulfides 12, 13, respectively. In the presence of a palladium catalyst, the salt 2e underwent the Heck-type reaction with ethyl acrylate 17 to afford the dienoate 18 and cinnamate 19 in moderate yields. Action of KOBut on the salt 2b yielded p-tolylacetylene 22, while a similar reaction with the salt 2e in the presence of the styrenes 23 gave the cyclopropanes 24. A Hammett study of the latter reaction has suggested a possible involvement of an alkylidenecarbene as the intermediate in these base-promoted reactions.
View MoreNanjing Chemlin Chemical Co., Ltd.
website:http://www.echemlin.cn
Contact:+86-25-83697070
Address:Rm.902 Longyin Plaza, No. 217 Zhongshan Rd.(N) Nanjing 210009,China
Contact:21-7631221 15884421033
Address:326 Science and technology,Shanghai,China
Shanghai Kefu Chemical Co.,Ltd.
Contact:+86-21-34616196
Address:Room601-602, Xuhui Business Building, No.168, Yude Road, Shanghai
Changzhou Qidi Chemical Co., Ltd
website:http://www.czqdhg.com/
Contact:86-519-83382137
Address:128-1-16# HuaYuan Street,Hutang Town,Wujin District,Changzhou City,P.R.China.
Evergreen Chemical Industry Ltd.
Contact:86-553-4918210
Address:6#2-602 Wanhaobailing
Doi:10.1021/ma0496652
(2004)Doi:10.1002/ejic.202000805
(2020)Doi:10.1016/0040-4020(96)00782-X
(1996)Doi:10.1016/0040-4039(96)01749-2
(1996)Doi:10.1021/jm960305h
(1996)Doi:10.1021/jo00377a030
(1987)
