PEYOTE (Hive Bee)
10-04-01 04:29
No 220202
       Cleavage of oximes to C=O compounds w Mn(OAc)3  Bookmark   

I've found on Tetrahedron Lett. 38, (1997), 7276 a method for the cleavage of oximes to carbonyl compounds using Mn(OAc)3 in benzene under reflux.

Globally:

2R2C=NOH + 2Mn(OAc)3 =(benzene)=> 2R2CO + 2Mn(OAc)2(ppt) + 2AcOH + N2

Yields are guaranteed between 86 and 96%. Time of reflux between 30 min. and 2 h.

Other methods of cleavage:

JOC 51, (1986), 3063 (using CTAP = cetyltrimetylammonium permanganate)
Tetrahedron Lett. (1971), 195 (using Ti3+)
JOC 31, (1966), 3446 (using bisulphite) 		 
 
 
 
    Osmium
(Stoni's sexual toy)
10-04-01 07:15
No 220228
       Re: Cleavage of oximes to C=O compounds w Mn(OAc)3  Bookmark   

What´s wrong with acid hydrolysis? Will the yields be lower? 		 
 
 
 
    PEYOTE
(Hive Bee)
10-04-01 11:36
No 220301
       Re: Cleavage of oximes to C=O compounds w Mn(OAc)3  Bookmark   

No, it was another use of this chemical; havent you seen Post 205055 (Antoncho: "P2Ps from benzene, acetone and Mn(AcO)3", Novel Discourse)? 		 
 
 
 
    Osmium
(Stoni's sexual toy)
10-04-01 13:02
No 220339
       Re: Cleavage of oximes to C=O compounds w Mn(OAc)3  Bookmark   

You confuse me. 		 
 
 
 
    foxy2
(Distinctive Doe)
10-04-01 22:29
No 220544
       Re: Cleavage of oximes to C=O compounds w Mn(OAc)3  Bookmark   

You can also epoxidize olefins with it.
Do Your Part To Win The War 		 
 
 
 
    PEYOTE
(Hive Bee)
10-05-01 02:35
No 220617
       Re: Cleavage of oximes to C=O compounds w Mn(OAc)3  Bookmark   

It can also be used for chlorination of alkenes (with acetic acid) -> Tetrahedron Lett. 26(6) (1984) 607   and as oxidant agent -> Wiad. Chem. (I dunno what journal it is) 30(10) (1976) 659.