674785-05-8Relevant academic research and scientific papers
An unusually robust triple bond: Synthesis, structure and reactivity of 3-alkynylcyclopropenes
Gilbertson, Robert D.,Wu, He-Ping,Gorman-Lewis, Drew,Weakley, Timothy J.R.,Weiss, Hans-Christoph,Boese, Roland,Haley, Michael M.
, p. 1215 - 1223 (2004)
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.
