Ring-fused gem-Dibromocyclopropanes as Precursors to "Tunable" Molecular Clefts Possessing Convergent Functional Groups

Abstract

Reaction of certain ring-fused gem-dibromocyclopropanes with methyllithium affords syn-cyclopropylidene dimers such as 2 which contain converging and potentially co-ordinating groups. Cyclofunctionalisation of the double bonds within these latter compounds allows the "angle-of-bite" between the co-ordinating groups to be "tuned" such that, under electrospray conditions in the mass spectrometer, derivative 7 forms a 1:1:1 complex with, for example, D-ribose and sodium ion.