Possible answer to Sam's question
One of our loyal blog readers, Sam, wished to know how primary alcohols were iodinated using triphenylphosphine, iodine and imidazole. Here is it, courtesy of petr:
In any case have fun in the thursday morning seminars, Samuel! I wish I was there to see a certain first year PhD student write his messy structures (if you can call them that) on the board together with sound effects. Bob Woodward would surely be turning in his grave!-Bkr
posted by Bunsen and Beaker @ 9:24 AM
94 Comments:
Hi Beaker,
I guess the mechanism is somewhat different. It resembles Apple reaction.
Thanks Petr,
I guess I should stick to inorganic chemistry! (I'll fix the pic)
Hmmmm, I guess you should probably put a lone pair on the P and N....
...ummm...yeah...whatever. Was lazy.
Aw, Beaker, thanks for your help!
Cheers,
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ummmm......what's a mechanism?
you really shouldn't deprotonate your alcohols with imidazole, look at the pkas
It's probably a deprotonation once the alcohol has coordinated to the positively charged phosphine. Otherwise the pka's are not so hot.
who doesn't love a bit of chemical mechanism rhapsody?
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Oh Boo Hiss! I posted a similar reply to the same poster (Sam) over at my little blog... just without the figure.
Anywho, you don't need the imidazole, it works fine with I2 and TPP. I think NIS works as well.
I'll think about u guys every thursday now at 10am whilst i'm enjoy morning tea. Earl grey or english breakfast?
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