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phenylnitroalkenes ---(Pb/DMF-AcOH)---> oximes

Started by Azarius, May 14, 2002, 08:06:00 PM

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Azarius

In

Post 242123

(Cyrax: "Re: Synthesis of amphetamines", Methods Discourse)
, Cyrax quotes a procedure for the conversion of phenylnitroalkenes to the corresponding acetoximes and ketoximes. Has anyone tried this procedure? Am I mistaken in thinking this looks like the easiest, fastest, high-yielding way of preparing oximes from phenylnitroalkenes? Any help greatfully appreciated.

Azarius

kurupira

This one uses Na2SnO2 made in situ, and yields are good:

Post 70461 (missing)

(yellium: "Tet. Lett. 26(49), 6013-14 (1985)", Novel Discourse)

Rhodium

Apparently that procedure is only good for small quantities, at least using straight SnCl2:

Post 192513 (missing)

(Ritter: "Re: solubility of SnCl2 in H2O", Chemistry Discourse)

kurupira

Rhod:in the article above cited they use THF as the solvent, Ritter mentions EtOAc as solvent...

L.S.Dog!