[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

doi:10.1002/ejoc.201700946

[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

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	5410-5416
Nombre de pages	7
journal	European Journal of Organic Chemistry
Volume	2017
Numéro de publication	36
Les DOIs	https://doi.org/10.1002/ejoc.201700946
Etat de la publication	Publié - 2 oct. 2017

Accès au document

10.1002/ejoc.201700946

http://doi.wiley.com/10.1002/ejoc.201700946

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ejoc201700946
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CCDC 1539569: Experimental Crystal Structure Determination
Boldyreva, E. V. (Contributeur), Eltsov, I. V. (Contributeur), Nefedov, A. A. (Contributeur), Sagitullina, G. P. (Contributeur), Shuvalov, V. Y. (Contributeur) & Tumanov, N. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017
DOI: 10.5517/ccdc.csd.cc1np1jx, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1np1jx&sid=DataCite
Ensemble de données
CCDC 1539572: Experimental Crystal Structure Determination
Boldyreva, E. V. (Contributeur), Eltsov, I. V. (Contributeur), Nefedov, A. A. (Contributeur), Sagitullina, G. P. (Contributeur), Shuvalov, V. Y. (Contributeur) & Tumanov, N. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017
DOI: 10.5517/ccdc.csd.cc1np1m0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1np1m0&sid=DataCite
Ensemble de données
CCDC 1539571: Experimental Crystal Structure Determination
Boldyreva, E. V. (Contributeur), Eltsov, I. V. (Contributeur), Nefedov, A. A. (Contributeur), Sagitullina, G. P. (Contributeur), Shuvalov, V. Y. (Contributeur) & Tumanov, N. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017
DOI: 10.5517/ccdc.csd.cc1np1lz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1np1lz&sid=DataCite
Ensemble de données

Contient cette citation

@article{b85bcb7bf8e345b1857188ed90c3c92d,

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

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.",

keywords = "Aromaticity, Cyclophanes, N-Methylpyridinium salts, Nitropyridines, Rearrangement",

author = "Shuvalov, {Vladislav Yu.} and Eltsov, {Ilia V.} and Tumanov, {Nikolay A.} and Boldyreva, {Elena V.} and Nefedov, {Andrey A.} and Sagitullina, {Galina P.}",

note = "Funding Information: This work was supported financially by the Russian Foundation for Basic Research and Ministry of Education of Omsk Region (grant 16-43-550144/16 r_a). Publisher Copyright: {\textcopyright} 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

year = "2017",

month = oct,

day = "2",

doi = "10.1002/ejoc.201700946",

language = "English",

volume = "2017",

pages = "5410--5416",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

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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.

N1 - Funding Information: This work was supported financially by the Russian Foundation for Basic Research and Ministry of Education of Omsk Region (grant 16-43-550144/16 r_a). Publisher Copyright: © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2017/10/2

Y1 - 2017/10/2

N2 - 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.

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.

KW - Aromaticity

KW - Cyclophanes

KW - N-Methylpyridinium salts

KW - Nitropyridines

KW - Rearrangement

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U2 - 10.1002/ejoc.201700946

DO - 10.1002/ejoc.201700946

M3 - Article

SN - 1434-193X

VL - 2017

SP - 5410

EP - 5416

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 36

ER -

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

Résumé

Accès au document

Autres fichiers et liens

Document sous embargo

Empreinte digitale

Équipement

Physico-chimie et caractérisation (PC2)

Ensembles de données

CCDC 1539569: Experimental Crystal Structure Determination

CCDC 1539572: Experimental Crystal Structure Determination

CCDC 1539571: Experimental Crystal Structure Determination

Contient cette citation