S. Shaun Murphree

Synthesis of vinylic and cyclic sulfones via a radical addition-elimination sequence

Radical attack on the double bond of 2,3-bis(phenylsulfonyl)-1-propene leads to an intermediate sulfonyl stabilized radical. This species readily fragments to produce a new vinyl sulfone which can undergo further radical cyclization to give a six ring sulfone.

A new route to disubstituted cyclopentenones using 2,3-dibromo-1-(phenylsulfonyl)-1-propene as a pivotal reagent

2,3-Dibromo-1-(phenylsulfonyl)-1-propene acts as a dielectrophile towards 1,3-diketones and β-ketoesters providing an entry into a variety of 2,3-disubstituted cyclopentenones including cis-jasmone.