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Does 9-BBN not act on internal alkynes or alkenes?

  1. Jul 1, 2016 #1
    Organic Chemistry question! Is 9-BBN too sterically hindered to even react with internal alkynes or alkenes? (to do hydroboration)
     
  2. jcsd
  3. Jul 2, 2016 #2

    TeethWhitener

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    I've seen claims that 9-BBN can react with internal alkenes, but I haven't attempted it myself. I imagine the reaction would take longer than a reaction with a terminal alkene. The goal of the big substituents is to favor boron addition at less sterically hindered sites with high regioselectivity. 9-BBN generally tends to be more regioselective than something like borane-THF. You can also get it in solid form, which is easier to use than gaseous B2H6.
     
  4. Jul 3, 2016 #3
    Thanks!
     
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