Metacyclophanes have been developed as non-planar aromatic compounds with unusual physical properties. –Metacyclophanes were synthesized by rearrangement of 3-nitro(perhydrocycloalka)[b]pyridinium salts, and analysis of their spectroscopic data and X-ray diffraction patterns indicates the aromaticity and flexibility of their benzene rings. The effectiveness and simplicity of the synthesis makes it possible to use them as available precursors in the synthesis of retinoids, indolophanes, and carbazolophanes.
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Shuvalov, V. Y., Eltsov, I. V., Tumanov, N. A., Boldyreva, E. V., Nefedov, A. A., & Sagitullina, G. P. (2017). -Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy. European Journal of Organic Chemistry, 2017(36), 5410-5416. https://doi.org/10.1002/ejoc.201700946