TY - JOUR A1 - Jurisch, Christopher D. A1 - Arnott, Gareth E. T1 - Attempted synthesis of a meta-metalated calix[4]arene JF - Beilstein Journal of Organic Chemistry PY - 2019/// VL - 15 SP - 1996 EP - 2002 SN - 1860-5397 DO - 10.3762/bjoc.15.195 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.15.195 KW - calixarene KW - inherent chirality KW - mesoionic carbene KW - mononitration KW - ruthenacycle N2 - An evidence for the formation of a rare meta-metalated inherently chiral calix[4]arene is described. Our strategy involved using a mesoionic carbene to direct C–H activation, but proved to form an unexpectedly unstable intermediate that was identified through high-resolution mass spectrometry. On route to our target, a new optimized method to mononitrocalix[4]arenes was developed, including optimized and high yielding transformations to azide and 1,2,3-triazole derivatives which may have application in other areas of research. ER -