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Author: Subject: Solvent free oxime formation
GreenD
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[*] posted on 12-3-2012 at 06:04
Solvent free oxime formation


Was looking at various oxime formaton reactions (there aren't many!) and came across this interesting paper:

A solvent free reaction of hydroxylamine HCl and benzaldehyde in dry silica gel (by mechanical grinding).

http://www.tandfonline.com/doi/pdf/10.1080/00397919908086156

They also report that it is chemo-specific to aldehydes (no ketones).

Anyone read this before? I utfse and found nothing on here.




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Rich_Insane
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[*] posted on 20-3-2012 at 13:39


Have you seen: http://www.orgmedchemlett.com/content/pdf/2191-2858-1-12.pdf

They use Bi2O3 and dry grinding for production of oximes. It isn't specific for aldehydes, but they report that formation of the ketone oxime took longerv to complete. The aldoxime was generated by grinding NH2OH.HCl with Bi2O3 and extracting the resulting oxime with EtOAc.
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[*] posted on 22-3-2012 at 03:48


There are easier solvent free methods...

e.g. : http://www.organic-chemistry.org/abstracts/literature/153.sh...
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GreenD
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[*] posted on 22-3-2012 at 08:44


Wow.

I've actually heard trouble with this on a nother web site. Didn't look into it though.

[Edited on 22-3-2012 by GreenD]




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