Comparative stereochemistry of the fragmentations of oxychlorocarbenes, chlorocarbonates, and chlorosulfites in the 3-nortricyclyl/5-norbornen-2-yl system

Fragmentations of the title precursors in polar solvents proceed via similar ion pairs to mixtures of exo-2-chloro-5-norbornene and 3-nortricyclyl chloride. The stereochemical course of the conversions is mainly determined by least motion chloride return in ion pair intermediates.