Biochemical Reactions of Epoxides

Reaction 1. The rearrangement of an arene oxide gives a water-soluble phenol that is easily eliminated firom the body. Hence, this pathway does not lead to the accumulation of toxic by-products. 

Reaction 2. Ring opening of the arene oxide by water gives a trans diol by an Sj 2 process. The diol is water soluble and is also easily eliminated from the body. 

The epoxide metabolites of alkenes tend to be more stable than arene oxides. They undergo ring opening with water to give diols. One example of this type of reaction is the ring opening of the epoxide of the anticonvulsant drug carbamazepine. 

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