ORGLIST: amine N-oxide

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From: Witek Mozga (mozga$##$trimen.pl)
Date: Fri Apr 12 2002 - 01:56:44 EDT

Hi,

Has anyone worked with amine oxides? I just need some
comments and advices. I synthesized an oxide from a simple amine
and was astonished on its behavior. The amine dissolved in AcOEt
easily but when I added peroxyacetic acid two phases appeared. I
realize that amine oxides are dipolar species (similar to HMPA or
DMSO) but did not expect it to be immiscible with ethyl acetate.
What are your observations?

Another issue is removing oxygen atom from nitrogen in an amine
oxide. I planned to use the amine oxide as a temporary protecting
group for the amine in order to destroy its basicity. I`d like to
remove it later. I found that H2/Pd or SO2 can do the job. What
about phosphines? I don`t have access to Beilstein but I think I
remember that trivalent phosphorous has enormous affinity to
oxygen. Any suggestion?

Best Regards,

Witek
http://www.trimen.pl/witek/
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