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Author Topic: Cleavage of oximes to C=O compounds w Mn(OAc)3  (Read 2670 times)

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PEYOTE

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Cleavage of oximes to C=O compounds w Mn(OAc)3
« on: October 04, 2001, 04:29:00 AM »
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)
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Osmium

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Re: Cleavage of oximes to C=O compounds w Mn(OAc)3
« Reply #1 on: October 04, 2001, 07:15:00 AM »
What´s wrong with acid hydrolysis? Will the yields be lower?
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PEYOTE

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Re: Cleavage of oximes to C=O compounds w Mn(OAc)3
« Reply #2 on: October 04, 2001, 11:36:00 AM »
No, it was another use of this chemical; havent you seen

Post 205055

(Antoncho: "P2Ps from benzene, acetone and Mn(AcO)3", Novel Discourse)?
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Osmium

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Re: Cleavage of oximes to C=O compounds w Mn(OAc)3
« Reply #3 on: October 04, 2001, 01:02:00 PM »
You confuse me.
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foxy2

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Re: Cleavage of oximes to C=O compounds w Mn(OAc)3
« Reply #4 on: October 04, 2001, 10:29:00 PM »
You can also epoxidize olefins with it.
Do Your Part To Win The War
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PEYOTE

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Re: Cleavage of oximes to C=O compounds w Mn(OAc)3
« Reply #5 on: October 05, 2001, 02:35:00 AM »
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.
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