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.
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Doi:10.1002/anie.200601866
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(1983)
