SULFONATION OF ALKENES WITH SULFUR TRIOXIDE; REVERSIBLE STEREOSPECIFIC β-SULTONE FORMATION

Article abstract of DOI:10.1016/S0040-4039(01)80591-8

The small differences in the rate coefficients of β-sultone formation between the internal and the terminal double bond in the octenes 2a-c and (Z)-1,10-nonadecadiene are evidence for a concerted cycloaddition of sulfur trioxide.The formation of β-sultone 1d is accompanied by 15percent of 2-octene-1-sulfonic acid, formed in a primary side-reaction.The sulfonation of the octenes 2a-d to their β-sultones 1a-d is reversible.Desulfonation of the β-sultones 1a-d by water to the olefins 2a-d proceeds in a stereospecific syn fashion.