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Topic: Organic Reagents  (Read 3723 times)

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Offline harkkam

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Organic Reagents
« on: March 21, 2009, 03:17:09 AM »
I'm wondering how all of these reagents that are used today actually came about. I heard that some were mistakes, while some were made.

For example CrO3(Pyradine)2 will make a alcohol into a ketone. Collins Reagent.

Did somebody figure that out, discover it or invent it?

Is it possible to create new reagents, for example you study acidity and know that the acidic derivatives of sulfur are acidic.

So (CH3)2SO4 aka Dimethyl Sulfate, was that discovered by a scientist that when paired with a strong base that it can alkylate a negative oxygen atom.

Or did they know that by creating such a molecule that the properties of having four oxygen on the sulfur creates a stabilized anion allowing to alkylate.

I guess my question is if most reagents are discovered or invented.

Offline Borek

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Re: Organic Reagents
« Reply #1 on: March 21, 2009, 05:46:49 AM »
I guess my question is if most reagents are discovered or invented.

50/50

Well, probably not exactly 50/50. Trick is, some of these reagents were first discovered accidentally, then reaction conditions were fine tuned to increase usability. Thus they are hard to classify.
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Offline Arkcon

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Re: Organic Reagents
« Reply #2 on: March 21, 2009, 07:38:10 AM »
When I took organic chem, they were just handing out the Nobel Prize to the discoverer of crown ethers.  This was quite an interesting topic to my organic chem prof -- the ability of the crown ether to solubilize ionic salts, for example permanganate, is a tremendous boon to organic synthesis.  And what is it?  Just a bunch of repeated subunits, large enough to sequester a potassium ion, so permanganate comes along for the ride.  Subtle.  Genius.
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Offline Arkcon

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Re: Organic Reagents
« Reply #3 on: March 23, 2009, 07:35:27 PM »
Another story I'd heard -- sorry to be late, I had to check a reference I had at work -- was the Grubbs catalysts.  http://en.wikipedia.org/wiki/Olefin_metathesis#Grubbs_catalysts  As the story goes, the guy was filtering ruthenium trichloride, when it broke through the filter, past the receiving flask, and into the rubber vacuum hose.  Trying to reclaim the expensive reagent, he instead discovered the value of transition metal alkylidenes.
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