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Hettstedt, Christina; Heuschmann, Manfred; Karaghiosoff, Konstantin (2016): Synthesis and Halogen Bonding in the Crystal Structures of the New 2,3-Diiodo Indenone and 1-Ethoxy-2,3-diiodo Indene. In: Heteroatom Chemistry, Vol. 27, No. 2: pp. 75-82
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The CuI-catalyzed addition of iodine to the CC triple bond of 3,3-diethoxy-1-phenyl propyne (1) unexpectedly leads to the new cyclization products 2,3-diiodo-1H-inden-1-one (2) and 1-ethoxy-2,3-diiodo-1H-indene (3). Both compounds were isolated and characterized via H-1, C-13 NMR (Nuclear Magnetic Resonance) spectroscopy and HRMS (High Resolution Mass Spectrometry). The molecular and crystal structures of compounds 2 and 3 were determined by single crystal X-ray diffraction. Their crystal structures are governed by extensive halogen bonding, involving II and IO interactions.