An unusually robust triple bond: synthesis, structure and reactivity of 3-alkynylcyclopropenes

Several 1,2-diphenyl- and 1,2,3-triphenyl-3-alkynylcyclopropenes have been prepared in moderate to very good yields by the reaction of acetylenic nucleophiles with the appropriate cyclopropenylium salt. Single crystal X-ray structures of four of the cyclopropenes were obtained. Stereoselective reduction of the triple bond failed in all cases, whereas model compounds lacking the cyclopropene moiety were reduced successfully. A rational for this lack of reactivity is proposed. The solution-phase thermochemistry of the 3-alkynyl-1,2,3-triphenylcyclopropenes was explored, affording 3-alkynyl-1H-indenes in moderate to good yields.