130490-06-1Relevant articles and documents
Stereoselective synthesis of 1-bromo-1-fluorostyrenes
Shastin, Aleksey V.,Muzalevsky, Vasiliy M.,Balenkova, Elizabeth S.,Nenajdenko, Valentine G.
, p. 179 - 180 (2006)
The effective and stereoselective one-pot synthesis of 1-bromo-1- fluorostyrenes from aromatic aldehydes based on a catalytic olefination reaction was elaborated.
A kinetic separation method for the stereoselective preparation of 1-fluorovinylphosphonates from E/Z mixtures of 1-bromo-1-fluoroolefins
Zhang,Burton
, p. 47 - 54 (2001)
Reaction of E/Z mixtures of 1-bromo-1-fluoroolefins with diethylphosphite and catalytic Pd(PPh3)4 in triethylamine at 30-40°C gave predominately the (E)-isomer of the 1-fluorovinylphosphonate (E/Z ≥ 95:5) in good yields. Pure (E)-1-f
A kinetic separation method for the stereoselective preparation of (Z)- and (E)-monofluoroenynes from E/Z mixtures of 1-bromo-1-fluoroolefins
Zhang, Xin,Burton, Donald J.
, p. 317 - 324 (2007/10/03)
Reaction of E/Z mixtures of 1-bromo-1-fluoroolefins with 1-alkynes and catalytic Pd(PPh3)2Cl2 and CuI in triethylamine at room temperature gave (after 16-24h) predominately the (Z)-monofluoroenyne (Z/E>92/8) in good yields. Pure (Z)-monofluoroenyne could generally be obtained by chromatographic separation of the crude Z/E mixture. Pure (Z)-1-bromo-1-fluoroolefin could he recovered and reacted with 1-alkynes under similar conditions and longer reaction times (48h) to give pure (E)-monofluoroenynes in excellent yields (78-89%). Thus, E/Z mixtures of 1-bromo-1-fluoroolefins could be kinetically separated into (Z)- and (E)-monofluoroenynes. This methodology provides a simple one-step unequivocal route to the isomerically pure (Z)- and (E)-monofluoroenynes from the readily available 1-bromo-1-fluoroolefins.
