Preparation and reactions of 2-chloro-3,4-epoxy-1-butene: a convenient route to (Z)-3-chloroallylic alcohols.
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.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA. taberdf@udel.edu
Mitten
Jeffrey V
JV
D000438:Alcohols / Q000138:chemical synthesis*; D002073:Butanes / Q000138:chemical synthesis / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis*
C467960:2-chloro-3,4-epoxy-1-butene; D000438:Alcohols; D002073:Butanes; D004852:Epoxy Compounds; D006843:Hydrocarbons, Chlorinated