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« Silane (Weirdo methane) | Main | Propofol (Milk of Amnesia) »

Trimethyloxonium salts (When it absolutely, positively, must be methylated)

Category: Synthesis
Posted on: December 3, 2007 11:32 PM, by Molecule of the Day

When you take organic chemistry, you learn about methyl iodide for putting on a methyl group. Eventually, though, if you stick with chemistry, you need an alkylating agent for grown-ups.

There's a lot of good ones, including dimethyl sulfate, methyl triflate (PDF), and the ever-so-toxic "magic methyl," methyl fluorosulfonate.


Part of being a grown-up, though, is settling down with an alkylating agent, and aside from the odd dirty weekend with some of the more exotic compounds, it's trialkyloxonium salts for me:



We used to have coffee together in the morning, but the methanol got to me...

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Comments

1

"you need an alkylating agent for grown-ups."

I guess you're right. Time to grow up.

Posted by: Chemgeek | December 4, 2007 9:50 AM

2

You know, given the hazards inherent in methylating agents, I do believe you missed a chance at a primo Tarantino reference -- "when you absolutely, positively have to methylate every mofo in the room."

Posted by: Brian X | December 4, 2007 10:47 PM

3

there is a lovely method for making triethyloxonium tetrafluoroborate in Org Syn. You just mix together BF3 etherate, dry ether and epichlorohydrin. The stuff crashes out. I did it on a 50g scale.

You get trimethyl oxonium from triethyloxhonium just by blowing dimethylether gas stream over it. The alkyls exchange, bitches...

Posted by: milkshake | December 5, 2007 4:01 PM

4

"Mighty Methyl" I came across this in a search for a methylating agent. Pretty nifty. http://reedgrouplab.ucr.edu/projects/methyl.html

Posted by: Vince Noir | December 11, 2007 2:00 AM

5

What? No methyl lithium?

Posted by: Jenkins | December 17, 2007 2:19 PM

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