88652-80-6Relevant articles and documents
On the Preparation of (E)- and (Z)-Stilbene from the Diastereoisomeric 1,2-Diphenyl-2-diphenylphosphonoylethan-1-ols
Buss, Antony D.,Warren, Stuart,Leake, Jonathan S.,Whitham, Gordon H.
, p. 2215 - 2218 (1983)
(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.