Bicyclo[1.1.1]pentane Embedded in Porphyrinoids** |
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| Authors: | Dr. Nitika Grover Maxime Cheveau Dr. Brendan Twamley Dr. Christopher J. Kingsbury Cornelia M. Mattern Prof. Dr. Mathias O. Senge |
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| Affiliation: | 1. School of Chemistry, Chair of Organic Chemistry, Trinity Biomedical Sciences Institute, Trinity College Dublin, The University of Dublin, 152–160 Pearse Street, D02R590 Dublin, Ireland;2. School of Chemistry, Trinity College Dublin, The University of Dublin, Dublin 2, Ireland |
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| Abstract: | We report a two-step approach to obtain synthetically versatile bicyclo[1.1.1]pentane (BCP) derivatives using Grignard reagents. This method allows the incorporation of BCP units in tetrapyrrolic macrocycles and the synthesis of a new class of calix[4]pyrrole analogues by replacing two bridging methylene groups with two BCP units. In addition, a doubly N-confused system was also formed in the presence of electron-withdrawing substituents at the BCP bridgeheads. The pyrrole rings in BCP containing macrocycles exist in 1,3-alternate or αβαβ conformations, as observed from single-crystal X-ray diffraction analyses and 2D NMR spectroscopy. |
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| Keywords: | Bicyclo[1.1.1]Pentane Calix[4]Pyrrole Grignard Reagents Macrocycles Porphyrinoids |
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