Journal of Organic Chemistry p. 884 - 890 (1989)
Update date:2022-08-04
Topics:
Engman, Lars
Terminal and 1,2-disubstituted olefins were irreversibly acetoxyselenenylated by treatment with PhSeBr in an acetate buffer solution.Styrene derivatives yielded only Markovnikov adducts whereas simple terminal olefins and olefins containing an allylic oxygen substituent (acyloxy or aryloxy group) afforded significant amounts (50-85percent) of the anti-Markovnikov isomer.The product mixtures were isomerized to contain 90-97percent of the Markovnikov products by treatment with a catalytic amount (6-41percent) of BF3*OEt2 in chloroform.Oxidation (SO2Cl2/hydrolysis or MCPBA) of the isomerized products and selenoxide elimination at elevated temperature toward the acetoxy group afforded enol acetates in fair yields.The selenoxides of the anti-Markovnikov isomers (unisomerized mixtures) spontaneously eliminated, in the presence of the selenoxides of the Markovnikov isomer, to give allylic acetates in good yields at ambient temperature.
View MoreShanghai He Yang International Trading Co., Ltd.
Contact:+86-21-52043598
Address:Room 816, Blag.5, No.58 Huachi Road
website:http://www.sigmaaldrich.com
Contact:800 558-9160
Address:Industriestrasse 25CH-9471 Buchs SGSwitzerland
Contact:+86-519-86339586,13584329896
Address:Changzhou Scientific and Education Park
Anhui Sunsing Chemicals Co.,Ltd
website:http://www.sunsingchem.com
Contact:0086-566-2023179
Address:Jin An industry park, Chizhou economic technical development zone, Anhui
Suzhou Wedo Chemicals Co., Ltd.
Contact:86 512 58100425
Address:Zonger Road, DongSha Industry Park , Zhangjiagang, Jiangsu, China
Doi:10.1021/jo00269a036
(1989)Doi:10.3987/COM-09-11696
(2009)Doi:10.1248/cpb.57.826
(2009)Doi:10.1002/cbdv.200900039
(2009)Doi:10.1016/S0040-4039(00)80432-3
(1988)Doi:10.1016/j.tetlet.2009.08.102
(2009)