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Topic: Triethylsilane dehydroxylation  (Read 2382 times)

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Offline andeau

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Triethylsilane dehydroxylation
« on: October 08, 2017, 05:05:19 AM »
Hello everyone,
I need your help with a mechanism of a synthesis exercise I have to solve:

Starting from a tertiary alcohol and using Et3SiH with BF3-OEt2 in dichloromethane I am obtaining the alkane by eliminating hydroxyl group.

I have thought that maybe, the boron trifluoride diethyl etherate as a Lewis acid would remove the H from the silane leaving a negative charge on Si, and this one would bond the OH group.
Then the OH would be removed leaving a negative charge on the tertiary C, then the negative charge would bond the H from another molecule of silane, creating the alkane.

Do you think my mechanism could work, or did I make some mistakes?

Thank you in advance for any answer :)

Offline Babcock_Hall

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Re: Triethylsilane dehydroxylation
« Reply #1 on: October 09, 2017, 12:00:27 PM »
You are postulating that a Lewis acid acts as a base.

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