Journal of the Chemical Society. Perkin transactions I p. 2215 - 2218 (1983)
Update date:2022-07-29
Topics: Preparation Experimental Diastereoisomeric (Z)-Stilbene
Buss, Antony D.
Warren, Stuart
Leake, Jonathan S.
Whitham, Gordon H.
(1RS,2SR)-1,2-Diphenyl-2-diphenylphosphonoylethanol (erythro-isomer) (1) and its threo-isomer (2) have been prepared stereospecifically by opening the appropriate stilbene oxides with Ph2PLi followed by oxidation with H2O2-AcOH.Compounds (1) and (2) can also be obtained stereoselectively (erythro-isomer predominating) via treatment of Ph2POCHLiPh with PhCHO.Under all the conditions tried, treatment of the threo-isomer (2) with base gave (E)-stilbene.The erythro-isomer (1) under most conditions gave predominantly (E)-stilbene, together with variable amounts of Ph2POCH2Ph, through in one case mainly (Z)-stilbene was formed.The conversion erythro-(E)-stilbene was shown to occur via fragmentation to Ph2POCHLiPh and PhCHO by trapping experiments using m-chlorobenzaldehyde.
View MoreWUXI KINGHAN BIO-MEDICAL&CHEMICAL INC.
Contact:13861062998
Address:Room 1316,No.1619 Huishan Avenue,Wuxi,China
Contact:86-379-63338609
Address:Jiudian Village,Deting Town,Song County,Luoyang
Zhejiang Chemline International Co., Ltd.
Contact:+86-571-88062298
Address:Hengdian Industry Area, Dongyang, Zhejiang, China
Dalian Join King Biochemical Tech. Co., Ltd.
Contact:0411 39216206
Address:814 First State Blvd
Hunan Shineway Enterprise Co., Ltd.
Contact:+86-731-86303875
Address:118, Huanghua International Airport Road, Huanghua Town, Changsha, Hunan 410137, China
Doi:10.1002/anie.200601866
(2006)Doi:10.1016/j.ejmech.2017.03.013
(2017)Doi:10.1016/j.molcatb.2013.01.007
(2013)Doi:10.1016/S0040-4039(00)85925-0
(1983)Doi:10.1016/S0040-4020(01)91979-9
(1983)Doi:10.1016/S0040-4039(00)88418-X
(1983)
