33974-24-2Relevant articles and documents
cis-Bromination of a Non-conjugated Cyclic Alkene. Unprecedented Electrophilic Stereoselection by Means of a Remote SO2 Group
Cadogan, J. I. G.,Cameron, Donald K.,Gosney, Ian,Highcock, Rona M.,Newlands, Stephen F.
, p. 1751 - 1752 (2007/10/02)
Contrary to expectation, addition of molecular bromine to 3-thiabicyclohept-6-ene 3,3-dioxide (1) yields substantial amounts of the cis-1,2-dibromide (confirmed by X-ray diffraction), suggesting that the remote SO2 group exerts an extraordinary directive influence by means of a long-range Coulomb interaction that stabilises an open carbocation intermediate at the expense of the usually favoured bridged bromonium ion.