quantumcorespacealchemyst
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acetone hydrazone snthesis, selenone formation and haloformation of selenone of acetone
I may have a suitable lab setup this year to follow the synthesis of acetone hydrazine
http://www.orgsyn.org/demo.aspx?prep=cv6p0010
Please let me know what additional safety precautions to do in this preparation, and pointers.
I am interested in selonation. I read on http://en.wikipedia.org/wiki/Selenium_monochloride that " It converts hydrazones of hindered ketones into the corresponding selones, the
structural analogs of ketones whereby the oxygen atom is replaced with a selenium atom"
I know that it may not work, and have the idea to form an acetone selenone and use it in a haloform reaction to achieve an interesting salt.
Please let me know what you think about the possibility of these reactions. I don't know yet what a hindered ketone is and hope a suitable one can be
selonated and haloformed.
Thank you,
Ryan
[Edited on 16-2-2015 by quantumcorespacealchemyst]
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Dr.Bob
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I don't know anything about you lab or situation, but hydrazine is dangerous and anhydrous hydrazine is even more dangerous. It can be used and is a
great reagent, but I would work in a hood, with gloves and if you are handling the anhydrous material, it needs to be handled under nitrogen. If you
have a real use for acetone hydrazine, then that is likely a reasonable way to make it, but it seems like an odd compound to make.
Selenium compounds are another area I try to avoid, many selenium compounds are highly toxic, they smell bad, and while they are useful for some
oxidations, organo seleniums are not widely used.
Hindered ketones are ones with several alkyl groups near the ketone, just think of bulky substiuents. Usually hindered compounds are used when you
are trying protect a reactive piece from attach from another reagent.
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quantumcorespacealchemyst
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Thanks. I am thinking of using Helium in place of Nitrogen. I don't think that acetone hydrazine would be selonated anyway, but perhaps others can be.
I read there are sterically hindered methyl ketones. If these can be hydrazoned, and then selenoned with Selenium monochloride, they may be able to
make acid salts in the haloform reaction.
What I also don't know is if the selenones formed are Selenium bonded to two or one Oxygens.
On http://en.wikipedia.org/wiki/Methaneseleninic_acid
It says "Seleninic acids can be prepared by oxidation of selenoesters with one equivalent of dimethyldioxirane (DMDO). Use of excess DMDO affords
little studied selenonic acids (RSeO3H).
RSeC(O)R' + DMDO → RSeO2HRSeC(O)R' + excess DMDO → RSeO3H"
That seems interesting, the second case in exes DMDO, that is what I was aiming for from the
acetone--->azine--->hydrazone--->selenone---->haloform salt.
From this I wonder about further salts formed with the original idea using sterically hindered methyl ketones.
[Edited on 17-2-2015 by quantumcorespacealchemyst]
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