Stereochemically pure (E)-1-chloro(or bromo)alk-1-enes were obtained in sufficiently good yields from alk-1-ynes via hydroboration with dialkylborane followed by reactions with facile reagents; corresponding copper(II) halides, in the presence of a small amount of water, in polar aprotic solvents.
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Masuda et al. (1992) studied this question.
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