Azarius (Newbee)
05-14-02 20:06
No 308449
       phenylnitroalkenes ---(Pb/DMF-AcOH)---> oximes  Bookmark   

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
(Stranger)
05-15-02 14:37
No 308763
       ref  Bookmark   

This one uses Na2SnO2 made in situ, and yields are good: Post 70461 (yellium: "Tet. Lett. 26(49), 6013-14 (1985)", Novel Discourse) 		 
 
 
 
    Rhodium
(Chief Bee)
05-15-02 20:29
No 308876
       Oximes using SnCl2  Bookmark   

Apparently that procedure is only good for small quantities, at least using straight SnCl2: Post 192513 (Ritter: "Re: solubility of SnCl2 in H2O", Chemistry Discourse) 		 
 
 
 
    kurupira
(Stranger)
05-16-02 02:34
No 308999
       maybee the solvent...  Bookmark   

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