[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 journalArticle

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.
LanguageEnglish
Pages5410-5416
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number36
DOIs
StatePublished - 2017

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nuclear magnetic resonance
crystal structure
synthesis
spectroscopy
Ultraviolet spectroscopy
Nuclear magnetic resonance spectroscopy
Crystal structure
aromatic compounds
flexibility
diffraction patterns
physical properties
benzene
salts
rings
x rays
Aromatic compounds
Retinoids
Benzene
Diffraction patterns
Physical properties

Cite this

Shuvalov, V. Y., Eltsov, I. V., Tumanov, N. A., Boldyreva, E. V., Nefedov, A. A., & Sagitullina, G. P. (2017). [6]-[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy. European Journal of Organic Chemistry, 2017(36), 5410-5416. DOI: 10.1002/ejoc.201700946
Shuvalov, Vladislav Yu. ; Eltsov, Ilia V. ; Tumanov, Nikolay A. ; Boldyreva, Elena V. ; Nefedov, Andrey A. ; Sagitullina, Galina P./ [6]-[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 36. pp. 5410-5416
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Shuvalov, VY, Eltsov, IV, Tumanov, NA, Boldyreva, EV, Nefedov, AA & Sagitullina, GP 2017, '[6]-[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy' European Journal of Organic Chemistry, vol 2017, no. 36, pp. 5410-5416. DOI: 10.1002/ejoc.201700946

[6]-[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy. / Shuvalov, Vladislav Yu.; Eltsov, Ilia V.; Tumanov, Nikolay A.; Boldyreva, Elena V.; Nefedov, Andrey A.; Sagitullina, Galina P.

In: European Journal of Organic Chemistry, Vol. 2017, No. 36, 2017, p. 5410-5416.

Research output: Contribution to journalArticle

TY - JOUR

T1 - [6]-[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy

AU - Shuvalov,Vladislav Yu.

AU - Eltsov,Ilia V.

AU - Tumanov,Nikolay A.

AU - Boldyreva,Elena V.

AU - Nefedov,Andrey A.

AU - Sagitullina,Galina P.

PY - 2017

Y1 - 2017

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AB - 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.

U2 - 10.1002/ejoc.201700946

DO - 10.1002/ejoc.201700946

M3 - Article

VL - 2017

SP - 5410

EP - 5416

JO - European Journal of Organic Chemistry

T2 - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

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Shuvalov VY, Eltsov IV, Tumanov NA, Boldyreva EV, Nefedov AA, Sagitullina GP. [6]-[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy. European Journal of Organic Chemistry. 2017;2017(36):5410-5416. Available from, DOI: 10.1002/ejoc.201700946