ORGLIST: t-BuOOH and VO(acac)2 epoxidation

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From: Oleg Nadein (nadein$##$
Date: Thu Apr 28 2005 - 19:47:47 EDT

Hi everybody

We are doing epoxidation of a cyclic olefine in our lab using t-BuOOH
and VO(acac)2 (epoxidation directed by a hydroxyl) and having some
problems - it does not work. We cannot reproduce it even with simple
compounds and must be doing something completely wrong. (30% t-BuOOH was
used in one reaction and 2% t-BuOOH in toluene in another one).

It seems to me that catalyst is quenched in the course of the reaction
(it changes color green to red then back to dirty green) - probably by
water in the reaction mixture. Mo(CO)6 can be used also for the same
purpose but we haven't tried it yet.

So I wanted to ask if anybody has experience with that reaction, knows
any features or specific requirements to chemicals etc.

Also if anybody has other noteworthy information on epoxidation of
olefins directed by -OH group - let me know.

Oleg N. Nadein
Chemistry Department
New Mexico Tech
801 Leroy Place
Socorro, NM 87801

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