Vibrating_Lights (Hive Addict)
07-08-02 18:51
No 330171
      Solvent free permanganate oxidation of isosafrole  Bookmark   

Could the solvent free permanganate oxidation with KMnO4/Cuso4 be used with isosafrole to obtain the epoxide or ketone?
Tetrahedron Letters 43(2001) 5833-5836
(Bee without a Title)
07-08-02 19:52
No 330197
      i think that will give you heliotropin  Bookmark   

i think that will give you heliotropin
(Hive Addict)
07-08-02 20:26
No 330211
      The copper is a catalyst  Bookmark   

True a typical permanganate oxidation would probably give helitropin but I think the copper acts as a catalyst in this reaction to oxidise in a different manner???????/
fluorene is oxidised to fluorone but it it appears to oxidise  the fluorene at a 9 position which is the only point without a double bond i think. It seems that double bonds are not oxidised.  With safrole the double bond is at the 1 position correct so In theory the 2 position would be oxidised if consistant with the fluorene oxidation.  But then how would the double bond be gotten rid of and the nescesary H added to complete the methyl group conversion to isosafrole usually leaves the methyl proper when the bond is moved?????.
(Chief Bee)
07-08-02 21:54
No 330269
      doesn't work  Bookmark   

The reaction only works in the benzylic position on alkylbenzene substrates.
(Hive Addict)
07-09-02 10:43
No 330454
      RXN 14  Bookmark   

IN Rxn 14 i the publication
4-methoxybenzyl alcohol, a primary alcohol, is oxidised to 4-anisealdehyde in a 95% yeild with 45mins of rxn time employing a mix of permanganate and alumina.  Is it reasonable to assume that ephedrine would be oxidised in a similar manner with possibly higher yeilds since the yeild loss with the 4-anisealdehyde was probably due in part but the cleavage of the Methoxy on the ring which ephedrine doesnt have.  the 45 min rxn time also is appealing since Meth cat free base is supposed to have the tendancy to dimmerise apoun standing.
 Has any one ever tried to reductivly aminate methcat