November 13, 2019, 06:50:47 PM
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Topic: Disiamylborane  (Read 300 times)

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Offline sharbeldam

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Disiamylborane
« on: June 07, 2019, 01:20:06 PM »
Is it true that Disiamylborane (Sia2BH) only reacts with terminal alkynes to produce aldehydes? it does not react with internal alkynes? and if I need to convert terminal alkynes to aldehydes, must i use the Sia2BH reagent? or would the normal B2H6 (hydroboration) work as well?

Thanks
« Last Edit: June 07, 2019, 01:38:24 PM by sharbeldam »

Offline sjb

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Re: Disiamylborane
« Reply #1 on: June 08, 2019, 02:41:03 AM »
Consider sterics and why Sia2BH might be effective. Compare to borane BH3

Offline sharbeldam

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Re: Disiamylborane
« Reply #2 on: June 08, 2019, 03:45:14 AM »
I tried, I cant tell whats the consequence of that though, I tried to search online but it does not show me the difference in the result

Offline sharbeldam

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Re: Disiamylborane
« Reply #3 on: June 08, 2019, 03:13:20 PM »
Because its more steric than borane it should be more selective for the terminal alkene but my question is, would it also react with an internal alkyne? and would a borane (BH3, normal hydroboration) react with a terminal alkene? or do we need the sterically hindered groups (alkyl or sia) attached to Boron for the terminal alkynes?

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