2,7-Di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxides: thermally stable, photochemically active vic-disulfoxides.
Bulking up: The thermal barrier to rearrangement of a vic-disulfoxide is significantly increased through steric buttressing about the (O)S--S(O) bond. Whereas the title compounds represent the most thermally stable vic-disulfoxides known to date, they also undergo a novel photomediated epimerization at room temperature (see scheme).
Grainger
Richard S
RS
School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK. r.s.grainger@bham.ac.uk
Patel
Bhaven
B
Kariuki
Benson M
BM
D018360:Crystallography, X-Ray; D007536:Isomerism; D008968:Molecular Conformation; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D010777:Photochemistry; D013458:Sulfur Dioxide / Q000737:chemistry*; D013696:Temperature
D010087:Oxides; D013458:Sulfur Dioxide