[akaEMILY]

B(CH3)3 + [(CH3)3C]2O

B(CH3)3 is a lewis acid.. I just don't understand why it wouldn't occur. Would it be too unstable to exist?

[akaEMILY]

Sorry about the repost. I posted this in general chem but realized I could get a more specific answer in organic.

B(CH3)3 + [(CH3)3C]2O

B(CH3)3 is a lewis acid.. I just don't understand why it wouldn't occur. Would it be too unstable to exist?

[Arkcon]

We don't need two. http://www.chemicalforums.com/index.php?topic=62723.0;topicseen So I will merge them.  But next time, akaEMILY: don't cross-post.

[Hunter2]

The ether is a big molecule. Probably steric problems.

[orgopete]

This is an interesting combination of effects. The chemistry of boron is consistent with becoming tetrahedral, for example boric acid B(OH)4(-) + H(+), BF4(-), BH4(-). That explains why trivalent boron compounds are Lewis acids. In this case, methyl groups are attached which donate electrons and reduce the Lewis acidity of boron.

Di-t-butylether is probably very easy to protonate and therefore generate a tertiary carbocation. Even with a weak Lewis acid, I might think B(CH3)3 would be sufficient to cleave t-butylether.

Could someone confirm the actual experiment results? What did or did not happen? How was the experiment done?

[orgopete]

I posted an answer in the general chemistry forum linked by Arkcon. I think this may have been a better topic in organic chemistry. Would it have formed a carbocation?