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

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 arom...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-10, Vol.2017 (36), p.5410-5416
Main Authors: Shuvalov, Vladislav Yu, Eltsov, Ilia V., Tumanov, Nikolay A., Boldyreva, Elena V., Nefedov, Andrey A., Sagitullina, Galina P.
Format: Article
Language:English
Subjects:
Aromatic compounds
Aromaticity
Benzene
Crystal structure
Cyclophanes
Diffraction
Diffraction patterns
Nitropyridines
NMR
Nuclear magnetic resonance
N‐Methylpyridinium salts
Physical properties
Rearrangement
Synthesis
X-rays
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Summary: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. Metacyclophanes have been developed as non‐planar aromatic compounds with unusual physical properties. Analysis of spectroscopic data and X‐ray diffraction of [6]–[8]metacyclophanes indicates the aromaticity and flexibility of their benzene rings.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700946