moonfisher
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Paper on cis-1,2 Cyclohexanediol
First, this easy and seemingly OTC method:
http://pubs.acs.org/doi/abs/10.1021/jo01098a606
It's even 1-pot!
Then, this science-direct paper (I have full access to this one!) with very high (too high?) yields from "the direct epoxidation and hydrolysis
(dihydroxylation) of cyclohexene to trans-1,2-cyclohexanediol, with an aqueous solution of hydrogen peroxide"
http://www.sciencedirect.com/science/article/pii/S0926860X13...
Might be interesting for yall. I am suspicious of the reported yields for paper 2.
Well, good chemists shouldn't lick their fingers, anyways
-Life advice from Sir Martyn
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Dr.Bob
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The first is a classic method, the second article I can't access from home. Doing the reaction with KMnO4 would also be more practical for home
chemists. OsO4 also would work catalytically, but is a bit toxic for home use. But peroxide would be nice from an atom efficiency point of view.
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moonfisher
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Quote: Originally posted by Dr.Bob  | | The first is a classic method, the second article I can't access from home. Doing the reaction with KMnO4 would also be more practical for home
chemists. OsO4 also would work catalytically, but is a bit toxic for home use. But peroxide would be nice from an atom efficiency point of view.
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I've read about the base mech. for the first paper, but never actually seen it used in a synth. Woodward cis-hydroxylization iirc?
>>OsO4
>>"a little toxic"
Would you like a pdf of the paper?
Well, good chemists shouldn't lick their fingers, anyways
-Life advice from Sir Martyn
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Dr.Bob
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Few people use the Woodword method now, as it uses a huge amount of reagent for a small amount of substrate, and MnO4 or OsO4 are both likely cheaper
and simpler. I looked at the paper at work, and it does not look that exciting. People have done opening of epoxides to trans-diols since I was in
school (that is a long time ago...) and the hydrogenation gives a mixture of cis and trans, which does not seem to be well quantitated in the paper.
If they had found a way to get selectively cis, that would have been more useful, although for making adipic acid, it may not matter. But again,
reducing benzene to cyclohexane is not that novel either, just takes some heat and pressure, less so with better catalysts. Few home chemists have a
Parr system available, sadly.
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