THE FIRST EXAMPLE OF ADDITION OF A 1,2-DICATION TO A C-C MULTIPLE BOND - REACTION OF S-S DICATIONS WITH ALKENES AND ALKYNES

The reactions of a bicyclic dithioether dication, generated from 1,4-d ithiane 1-oxide, with a carbon-carbon multiple bond proceed as conjuga ted addition of two sulfonium groups and gives rise to derivatives of dithioniabicyclo[2.2.2]octane. The reaction is sensitive to electronic and steric factors. In all cases investigated the reactions of 1,2-di substituted arylalkene proceed with retention of the relative arrangem ent of substituents at the double bond of the original alkene. A possi ble explanation of the obtained results is discussed.