April 20, 2024, 11:44:05 AM
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Topic: mCPBA Epoxidation  (Read 21381 times)

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Offline Qfbale

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Re: mCPBA Epoxidation
« Reply #15 on: April 20, 2016, 04:01:35 PM »
As Orgopete said, that is what I do for epoxides.

If you would like to try it, I have a procedure I use that you can follow.

Let me know.  It is high yielding.


I'm having the same problem epoxides, when I reaction , got several products , one majority . Then I purified and got 4 compounds , none corresponded to epoxidized compound I wanted , were derived from MCPBA .
Any recommendation?

Offline orgopete

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Re: mCPBA Epoxidation
« Reply #16 on: April 21, 2016, 04:03:27 PM »
Can you show the reaction?
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Offline Dan

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Re: mCPBA Epoxidation
« Reply #17 on: April 22, 2016, 02:38:44 AM »
Then I purified and got 4 compounds , none corresponded to epoxidized compound I wanted , were derived from MCPBA .
Any recommendation?

If you can identify the products you have, you can figure out what the problem is and think about how it can be solved.

Common problems are unwanted oxidation of other functional groups or epoxide cleavage (by water, chlorobenzoic acid or neighbouring groups).

Acid-catalysed epoxide cleavage can often be suppressed by adding a weak insoluble base (e.g. bicarb) to neutralise the equivalent of chlorobenzoic acid produced in the reaction. Problems with neighbouring groups may require protection strategies. It's difficult to offer specific advice until there is enough data to diagnose the problem.
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