ChemChat

Mechanism:TFDO Epoxidation

Epoxidation of molecule 48 using triflurormethyl dioxirane (TFDO) to afford molecule 49 is a conserted reaction.

A student of mine made this awesome animation!

The artwork certainly looks impressive. But, we have to make sure the real chemistry is right.

Let's see...The proposed mechanism seem to start with the oxidizing reagent TFDO approaching the inactivated sp2C-H and then inserts an oxygen atom to the C=C. This confers an figure "8" intermediate during the transition state. Simultaneously, the oxygen dissociates from TFDO and forms an epoxide with the original C=C.

Sounds about right, right?

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