bfesser - 15-7-2009 at 19:14
So, I have triphenylmethanol and sodium tetraphenylboron, and was thinking how cool it would be to prepare the salt trityl tetraphenylborate. I was
thinking along the lines of dissolving the triphenylmethanol in concentrated sulfuric acid to form the trityl carbocation and then adding the
tetraphenylboron reagent to it somehow.
A quick google search later, and I've found that it is prepared via trityl triflate--not really accessible for me at the moment. Obviously, if it
were possible to synthesize it using a relatively cheap reagent such as sulfuric acid rather than an exotic and expensive triflate reagent, it would
have shown up in the literature search. So I decided to search for the MSDS of my sodium tetraphenylboron and noticed in it that acids are listed as
incompatibilities. Good thing I didn't experiment before Googling it first, I guess.
I have three questions, as follows:
1. What reaction(s) occurs between tetraphenylborate and acids?
2. Does anyone have any thoughts or ideas as to how to synthesize this compound?
3. Does anyone have any other recommendations as to what I can do with my sodium tetraphenylboron?
Klute - 15-7-2009 at 20:12
You can prepare trityl chloride by refluxing trityl alcohol in acetyl chloride. I would then use this in place of the triflate to alkylzte the boron.
You could also form the mesyklate of tosylate depending on what you have access to.
My guess is rupture of the C-B bond in strong acids, forming a boronic acid and benzene.