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October 11, 2005
The Old Stuff
I was telling a story the other day about using a reagent called PCC, pyridinium chlorochromate and yes, I'm a real laugh riot with these things, when it hit me: nobody much uses that stuff any more. Twenty, twenty-five years ago it was all over the place, and now it's slipping into history. I haven't used it myself in what - eight years or so. There are too many other reagents that do similar things and are easier to clean up (and that don't involve so much chromium waste).
Organic chemistry is littered with reactions that have been superseded. You don't see many Oppenauer oxidations these days ,for one. (I know that if you follow that link it gives you a 2002 reference. But it's for a reaction that about a dozen things would do just as easily, at least on a bench scale.) How about the Rosenmund reduction? Such things show up once in a while in carefully optimized process chemistry routes, but they're no longer part of anyone's normal tool kit. Does anyone use manganese dioxide much these days, or potassium permanganate? (That last one is a real loss, one of the most beautiful purples in all of chemistry - it and copper sulfate were my first loves when I got a chemistry set as an eight-year-old.)
But simultaneously, there are hundred-year-old reactions that are still getting up in the morning and going to work. Grignard reagents go back that far, and there's not an organic synthesis lab on Earth that doesn't use one once in a while. The Dieckmann condensation is still going strong, as is Fischer esterification. It would be worth knowing which category is better-remembered today: novels from the 1890s, or chemical reactions. . .
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