Attempted synthesis of a meta-metalated calix[4]arene

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.