ORGLIST: Re: Oxidative cleavage of alkenes

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From: alihoyer$##$post.uni2.dk
Date: Mon Aug 09 1999 - 16:57:32 EDT

Permanganate is not often used synthetically due to its low
solubility in organic solvents. However, even sensitive substrates
may be selectively oxidized. Some of the D Vitamins are selectively
oxidized in a dihydroxylation of the conjugated triene system which
takes place at the trisubstituted 7,8 double bond in preference to
the trisubstitued 5,6 double and the exocyclic disubstituted 10,19
double bond. Cleavage of the resulting 1,2 glycol requires stronger
oxidants.

Thomas Hoyer

> In reply to:
>
> >Why is the use of permanganate not advisable?
> >Please enlighten me further.


> The above indicate the vigorous nature of permanganate oxidations, which
> make it less suitable for specific synthetic steps.

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