Mislow-Evans rearrangement

What is Mislow-Evans rearrangement?

Mislow-Evans rearrangement is a [2,3]-sigmatropic rearrangement of allylic sulfoxides to allylic sulfenates which are captured by thiophiles to yield the allylic alcohols. Thus, effecting the 1,3-transposition of sulfoxide and alcohol functions.

Mislow–Evans rearrangement - general reaction scheme
Mislow-Evans rearrangement

The reverse process is carried out by treating the alcohol with arylsulfenyl chloride, followed by thermal rearrangement of the sulfenate to generate the allylic sulfoxide.

References

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