1. Jul 1, 2016 #1

   fangrz

   

   Organic Chemistry question! Is 9-BBN too sterically hindered to even react with internal alkynes or alkenes? (to do hydroboration)

    

   fangrz, Jul 1, 2016
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3. Jul 2, 2016 #2

   TeethWhitener

   

   Science Advisor

   Gold Member

   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.

    

   TeethWhitener, Jul 2, 2016
4. Jul 3, 2016 #3

   fangrz

   

   Thanks!

    

   fangrz, Jul 3, 2016

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