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The Hive => Methods Discourse => Topic started by: Azarius on May 14, 2002, 08:06:00 PM

Title: phenylnitroalkenes ---(Pb/DMF-AcOH)---> oximes
Post by: Azarius on May 14, 2002, 08:06:00 PM
In

Post 242123 (https://www.thevespiary.org/talk/index.php?topic=9092.msg24212300#msg24212300)

(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
Title: ref
Post by: kurupira on May 15, 2002, 02:37:00 PM
This one uses Na2SnO2 made in situ, and yields are good:

Post 70461 (missing)

(yellium: "Tet. Lett. 26(49), 6013-14 (1985)", Novel Discourse)
Title: Oximes using SnCl2
Post by: Rhodium on May 15, 2002, 08:29:00 PM
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)
Title: maybee the solvent...
Post by: kurupira on May 16, 2002, 02:34:00 AM
Rhod:in the article above cited they use THF as the solvent, Ritter mentions EtOAc as solvent...
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