Preparation and reactions of 2-chloro-3, 4-epoxy-1-butene: a convenient route to (Z)-3-chloroallylic alcohols
DF Taber, JV Mitten
Index: Taber, Douglass F; Mitten, Jeffrey V The Journal of organic chemistry, 2002 , vol. 67, # 11 p. 3847 - 3851
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Citation Number: 11
Abstract
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/SMe2-mediated SN2'addition of sp2-or sp3-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.
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[Shellhamer, Dale F.; Green, Richard C.; Luttrull, Jeffrey K.; Seneker, Stephan D.; Potter, Mark K.; et al. Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 229 - 232]