xxxxx - 1-2-2008 at 10:33
a paper describing the formation of sodium nitromethane and adding to halogen on carbon is attached. maybe this could be a useful aternative to
requiring aldehydes and ketones to add nitromethane to a molecule.
PainKilla - 1-2-2008 at 10:47
Might you know from where that is?
It does seem useful, except as far as I remember, the aliphatic nitro salts are explosive and not very stable.
Also, is sodium absolutely necessary? I suppose it can be generated in situ with NaOH and nitroethane, but I am sure that will not work
nearly as well (if at all).
Also, 83% yield? It seems the yield is around 60%....
[Edited on 1-2-2008 by PainKilla]
Nicodem - 1-2-2008 at 13:41
That is from:
Synthesis of paredrine and related compounds.
Hoover F.W., Hass H.B.
J. Org. Chem., 12 (1947) 501.
xxxxx, it is considered very impolite and deceiving to post one page of a paper without providing the reference, especially if
on the previous page is explained that alkylation of nitroethane only works with benzyl chlorides substituted with strongly electron withdrawing
groups like the -NO2!
PainKilla - 1-2-2008 at 14:48
Thanks Nicodem!
That definitely does limit the usefulness of the reaction... though it still is interesting...
The full paper is attached for anyone interested in the (full) article.
[Edited on 1-2-2008 by PainKilla]
Attachment: SYNTHESIS OF PAREDRINE AND RELATED COMPOUNDS.pdf (360kB)
This file has been downloaded 527 times
chemrox - 1-2-2008 at 15:20
This is the second one of these scanned papers, turned sideways and without refs, today. Please at least give the cite so we can look it up and post
the link. Thank you PainKilla for taking care of this one. In future please post a link to the full paper or quote and cite like a professional.