Reactions of 9,9′‐bibenzonorbornenylidene sulfoxides with TMSOTf: Anomalous pinacol‐type rearrangement of thiirane 1‐Oxides

Abstract

syn-9,9 -Bibenzonorbornenylidene sulfoxide 8b underwent pinacol-type rearrangement to form 9, together with a mixture of thiiranes 4a and 4b by reaction with TMSOTf in CH 2 Cl 2 at room temperature. The rearrangement of anti-sulfoxide 8a proceeded more slowly giving a mixture of 9, 4a, and 4b.