Sulfonyl group 1,3-rearrangement

Rearrangements of this type are unifold transformations, which show [l.n]shifts of the sulfonyl group within the carbon moiety. 

Photo-Fries Rearrangement and Related Photochemical [l,j]-Shifts (j = 3,5, 7) of Carbonyl and Sulfonyl Groups... 

The Smiles-type rearrangement of phenyl o-tolyl sulfone [222] has been shown to proceed via an addition-elimination pathway by isolation of the tricyclic intermediate. Both sites of deprotonation and addition are controlled by the sulfonyl group with contrapolarization at the second stage. 

Bucher, G., Strehl, A., Sander, W. Laser flash photolysis of disulfonyidiazomethanes Partitioning between hetero-Wolff rearrangement and intramolecular carbene oxidation by a sulfonyl group. Eur. J. Org. Chem. 2003, 2153-2158. 

The nucleophile can be internally located on the vinylcyclopropane moiety as exemplified in the case of the anion-accelerated rearrangements of sulfonylvinylcyclopropanes of type 10. The resulting cyclopentenes can be further functionalized, through the agency of the sulfonyl group, in an overall four-step sequence from the starting diene. 

AJkenylsilanes and alkenyl sulfones. 1,1-Disilylepoxides undergo an unusual rearrangement, whereas p-silyl sulfones lose the sulfonyl group on treatment with LDA to give alkenylsilanes. - ... 

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