51830-18-3Relevant academic research and scientific papers
DIMETHYLALUMINIUM HALIDE INDUCED REACTIONS OF FORMALDEHYDE WITH ALKYNES. SYNTHESIS OF α-ALLENIC ALCOHOLS AND Z-3-CHLOROALLYLIC ALCOHOLS
Rodini, David J.,Snider, Barry B.
, p. 3857 - 3860 (1980)
The CH2O.Me2AlCl complex reacts with terminal alkynes to give α-allenic alcohols via a formal ene reaction and Z-3-chloroallylic alcohols via a stereospecifically syn Fridel-Crafts addition.
Preparation and reactions of 2-chloro-3,4-epoxy-1-butene: a convenient route to (Z)-3-chloroallylic alcohols.
Taber, Douglass F,Mitten, Jeffrey V
, p. 3847 - 3851 (2007/10/03)
Epoxide 2 was prepared from 3,4-dichloro-1-butene (1) by epoxidation with m-CPBA and subsequent dehydrohalogenation of the intermediate dichloroepoxide with molten KOH, affording 2 in 64% overall yield (2 steps). Catalytic CuBr/SMe(2)-mediated S(N)2' addition of sp(2)- or sp(3)-hybridized Grignard reagents to 2-chloro-3,4-epoxy-1-butene (2) afforded (Z)-3-chloroallylic alcohols such as 3 in good yields and with high regio- and stereoselectivity.
