[6]-[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy

Vladislav Yu. Shuvalov, Ilia V. Eltsov, Nikolay A. Tumanov, Elena V. Boldyreva, Andrey A. Nefedov, Galina P. Sagitullina

Research output: Contribution to journalArticlepeer-review

Abstract

Metacyclophanes have been developed as non-planar aromatic compounds with unusual physical properties. [6]–[9]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.
Original languageEnglish
Pages (from-to)5410-5416
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number36
DOIs
Publication statusPublished - 2 Oct 2017

Keywords

  • Aromaticity
  • Cyclophanes
  • N-Methylpyridinium salts
  • Nitropyridines
  • Rearrangement

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