Re: TOJC oxymucauratoin

Andrew Glandon (glandoal@plu.edu)
Thu, 05 Dec 1996 01:11:09 -0800 (PST)

On Wed, 4 Dec 1996 michelks@plu.edu wrote:

>
> One last question,
> It seems to me that it is possible to form a racemic solution in a
> oxymucuration-demurcuration rxn but the book doesn't explicitly say that.
> Can anyone confirm my gut feeling?
> Kevin Michels
>
Kevin-
I would say that this is possible. In my understanding of the reaction,
the mercury-bridged carbocation intermediate can form on either side of
the alkene C=C bond. If a stereocenter is formed via the addition of the
-OH group, I don't see any reason that the product could be a racemic. I
think this is right, but if I'm full of crap, somebody please tell me.

Andy Glandon