jwarr
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oxymercuration cosolvent choice
From what I've read, it seems the prototypical cosolvent for an oxymercuration reaction is THF. Since THF isn't readily available to me, I'm looking
for alternatives. Obviously alcohols are out of the question. I'm fairly certain ether would be fine, but I'd like to avoid distilling it from
starting fluid. Can anyone suggest another suitable cosolvent that is fairly easy for your average joe chemist to obtain? Am I right in thinking
that solubility in water and lack of acidity are the two major considerations?
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Nicodem
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You gave no references for what you read, so you will not obtain any proper answer.
| Quote: | | Since THF isn't readily available to me, I'm looking for alternatives. Obviously alcohols are out of the question. I'm fairly certain ether would be
fine, but I'd like to avoid distilling it from starting fluid. Can anyone suggest another suitable cosolvent that is fairly easy for your average joe
chemist to obtain? Am I right in thinking that solubility in water and lack of acidity are the two major considerations? |
Diethyl ether is unlikely to dissolve much of Hg salts though it depends on which salt you intent to use. THF is most certainly the simplest aplicable
solvent you can obtain. Solubility in water and lack of acidity of the solvent have nothing to do with oxymercuriations. Acetic acid is an acid and
yet it works fine for oxymercuriations where the acetoxy group is introduced. Acetonitrile works fine for introducing the acetamido group via
mercuriation. But since you don't say what you ask about, nobody can suggest you some alternative solvent instead of THF. You can try with 1,4-dioxane
though - often where THF works dioxane might also.
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jwarr
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| Quote: |
You gave no references for what you read, so you will not obtain any proper answer.
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My apologies.
The Oxymercuration-Demercuration of Representative Olefins. A Convenient, Mild Procedure for the Markovnikov Hydration of the Carbon-Carbon Double
Bond
J. Am. Chem. Soc., 1967, 89 (6), pp 1522–1524
The substrate is 2,4,5-trimethoxy-5-(2-propenyl)-benzene.
| Quote: | | Solubility in water and lack of acidity of the solvent have nothing to do with oxymercuriations |
Obviously I don't want something such as methanol in the solution competing with H2O for the addition. I guess what I am trying to avoid is
nucleophiles, not acids. Completely different, my mistake.
As for solubility in water, isn't it important that my substrate and the water attacking it be in the same phase? I've only got two semesters of
organic under my belt, so please if this is completely out of whack let me know.
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