Organic Letters

, volume 16 , issue 17 , pages 4532-4535

Photoinduced Skeletal Rearrangement of Diarylethenes Comprising Oxazole and Phenyl Rings

Andrey Lvov ¹

Valerii Z. Shirinian ¹

Vadim V. Kachala ¹

Alexey M Kavun ¹

Igor V. Zavarzin ¹

Mikhail M. Krayushkin ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

N. D. Zelinsky Institute of Organic Chemistry, RAS, 47, Leninsky prosp., 119991 Moscow, Russian Federation |

Publication type: Journal Article

Publication date: 2014-08-12

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/ol502073t

Copy DOI

PubMed ID: 25115452

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

A novel photochemical rearrangement of diarylethenes bearing oxazole and benzene derivatives as aryl moieties that results in the formation of polyaromatic systems was investigated. The mechanism of the transformation includes photocyclization, sequential [1,9] and [1,3]-hydrogen shifts, as well as a lateral oxazole ring-opening process. It was shown that this reaction can be an effective synthetically preparative method for the preparation of naphthalene (polyaromatic) derivatives.

Found

22 citations

Lvov Andrey

DSc in Chemistry

79 publications, 1 121 citations, 32 reviews

h-index: 20

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Irkutsk National Research Technical University

Research interests

Heterocyclic compounds

Organic Chemistry

Photochemistry

5 citations

Komogortsev Andrey

🥼 🤝

PhD in Chemistry

105 publications, 759 citations, 3 reviews

h-index: 15

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Photochemistry

5 citations

Melekhina Valeriya

PhD in Chemistry

57 publications, 413 citations

h-index: 12

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

Photochemistry

2 citations

Lyssenko Konstantin

🥼 🤝

DSc in Chemistry, professor

898 publications, 15 180 citations, 2 reviews

h-index: 50

Lomonosov Moscow State University

National Research University Higher School of Economics

Research interests

Supramolecular chemistry

2 citations

Lichitsky Boris

46 publications, 167 citations

h-index: 7

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Fershtat Leonid

DSc in Chemistry

147 publications, 2 994 citations, 121 reviews

h-index: 29

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Nelyubina Yulia

🤝

DSc in Chemistry

506 publications, 7 597 citations, 1 review

h-index: 38

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Moscow Institute of Physics and Technology

Metal-organic frameworks

Quantum technologies

Sensors

1 citation

Krylov Vadim

DSc in Chemistry

106 publications, 1 684 citations

h-index: 25

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Eliseev O

87 publications, 728 citations, 3 reviews

h-index: 17

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Peoples' Friendship University of Russia

1 citation

Kononov Leonid

DSc in Chemistry

150 publications, 2 085 citations, 28 reviews

h-index: 25

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Moscow Institute of Physics and Technology

1 citation

Nasyrova Darina

🤝

23 publications, 88 citations

h-index: 5

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Crystallography

X-ray diffraction (XRD)

X-ray diffraction analysis

1 citation

Stepanov Andrey

3 publications, 6 citations

h-index: 1

Irkutsk National Research Technical University

Research interests

Organic Chemistry

1 citation

Chaliy Vasiliy

🥼

7 publications, 19 citations

h-index: 3

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Bauman Moscow State Technical University

Research interests

Density functional theory (DFT)

Molecular modeling

1 citation

Sakharov Alexey

37 publications, 529 citations

h-index: 9

1 citation

Kodess Mikhail

PhD

298 publications, 2 827 citations

h-index: 25

Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Research interests

NMR spectroscopy

Top-30

Journals

	1 2 3 4 5 6 7 8 9
Journal of Organic Chemistry	Journal of Organic Chemistry, 9, 15.52% Journal of Organic Chemistry 9 publications, 15.52%
Organic Letters	Organic Letters, 7, 12.07% Organic Letters 7 publications, 12.07%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 6, 10.34% Organic and Biomolecular Chemistry 6 publications, 10.34%
Journal of Molecular Structure	Journal of Molecular Structure, 3, 5.17% Journal of Molecular Structure 3 publications, 5.17%
Tetrahedron	Tetrahedron, 2, 3.45% Tetrahedron 2 publications, 3.45%
Mendeleev Communications	Mendeleev Communications, 2, 3.45% Mendeleev Communications 2 publications, 3.45%
Chemistry - A European Journal	Chemistry - A European Journal, 2, 3.45% Chemistry - A European Journal 2 publications, 3.45%
RSC Advances	RSC Advances, 2, 3.45% RSC Advances 2 publications, 3.45%
Chemical Science	Chemical Science, 2, 3.45% Chemical Science 2 publications, 3.45%
Synthesis	Synthesis, 2, 3.45% Synthesis 2 publications, 3.45%
Journal of Physical Chemistry Letters	Journal of Physical Chemistry Letters, 1, 1.72% Journal of Physical Chemistry Letters 1 publication, 1.72%
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry	Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 1, 1.72% Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 1 publication, 1.72%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 1, 1.72% Chemistry of Heterocyclic Compounds 1 publication, 1.72%
Photochemical and Photobiological Sciences	Photochemical and Photobiological Sciences, 1, 1.72% Photochemical and Photobiological Sciences 1 publication, 1.72%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 1.72% Russian Chemical Reviews 1 publication, 1.72%
Dyes and Pigments	Dyes and Pigments, 1, 1.72% Dyes and Pigments 1 publication, 1.72%
Journal of Photochemistry and Photobiology A: Chemistry	Journal of Photochemistry and Photobiology A: Chemistry, 1, 1.72% Journal of Photochemistry and Photobiology A: Chemistry 1 publication, 1.72%
Tetrahedron Letters	Tetrahedron Letters, 1, 1.72% Tetrahedron Letters 1 publication, 1.72%
Journal of Photochemistry and Photobiology C: Photochemistry Reviews	Journal of Photochemistry and Photobiology C: Photochemistry Reviews, 1, 1.72% Journal of Photochemistry and Photobiology C: Photochemistry Reviews 1 publication, 1.72%
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 1, 1.72% Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 1 publication, 1.72%
ChemInform	ChemInform, 1, 1.72% ChemInform 1 publication, 1.72%
ChemCatChem	ChemCatChem, 1, 1.72% ChemCatChem 1 publication, 1.72%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 1, 1.72% Advanced Synthesis and Catalysis 1 publication, 1.72%
Journal of Physical Chemistry A	Journal of Physical Chemistry A, 1, 1.72% Journal of Physical Chemistry A 1 publication, 1.72%
Journal of the American Chemical Society	Journal of the American Chemical Society, 1, 1.72% Journal of the American Chemical Society 1 publication, 1.72%
Progress in Heterocyclic Chemistry	Progress in Heterocyclic Chemistry, 1, 1.72% Progress in Heterocyclic Chemistry 1 publication, 1.72%
Polycyclic Aromatic Compounds	Polycyclic Aromatic Compounds, 1, 1.72% Polycyclic Aromatic Compounds 1 publication, 1.72%
ChemistrySelect	ChemistrySelect, 1, 1.72% ChemistrySelect 1 publication, 1.72%
Synlett	Synlett, 1, 1.72% Synlett 1 publication, 1.72%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 1.72% European Journal of Organic Chemistry 1 publication, 1.72%
	1 2 3 4 5 6 7 8 9

Publishers

	2 4 6 8 10 12 14 16 18 20
American Chemical Society (ACS)	American Chemical Society (ACS), 19, 32.76% American Chemical Society (ACS) 19 publications, 32.76%
Elsevier	Elsevier, 11, 18.97% Elsevier 11 publications, 18.97%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 10, 17.24% Royal Society of Chemistry (RSC) 10 publications, 17.24%
Wiley	Wiley, 7, 12.07% Wiley 7 publications, 12.07%
Springer Nature	Springer Nature, 3, 5.17% Springer Nature 3 publications, 5.17%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 3, 5.17% Georg Thieme Verlag KG 3 publications, 5.17%
OOO Zhurnal "Mendeleevskie Soobshcheniya"	OOO Zhurnal "Mendeleevskie Soobshcheniya", 2, 3.45% OOO Zhurnal "Mendeleevskie Soobshcheniya" 2 publications, 3.45%
The Society of Synthetic Organic Chemistry, Japan	The Society of Synthetic Organic Chemistry, Japan, 1, 1.72% The Society of Synthetic Organic Chemistry, Japan 1 publication, 1.72%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 1.72% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 1.72%
Taylor & Francis	Taylor & Francis, 1, 1.72% Taylor & Francis 1 publication, 1.72%
	2 4 6 8 10 12 14 16 18 20

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Lvov A. et al. Photoinduced Skeletal Rearrangement of Diarylethenes Comprising Oxazole and Phenyl Rings // Organic Letters. 2014. Vol. 16. No. 17. pp. 4532-4535.

GOST all authors (up to 50) Copy

Lvov A., Shirinian V. Z., Kachala V. V., Kavun A. M., Zavarzin I. V., Krayushkin M. M. Photoinduced Skeletal Rearrangement of Diarylethenes Comprising Oxazole and Phenyl Rings // Organic Letters. 2014. Vol. 16. No. 17. pp. 4532-4535.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/ol502073t

UR - https://doi.org/10.1021/ol502073t

TI - Photoinduced Skeletal Rearrangement of Diarylethenes Comprising Oxazole and Phenyl Rings

T2 - Organic Letters

AU - Lvov, Andrey

AU - Shirinian, Valerii Z.

AU - Kachala, Vadim V.

AU - Kavun, Alexey M

AU - Zavarzin, Igor V.

AU - Krayushkin, Mikhail M.

PY - 2014

DA - 2014/08/12

PB - American Chemical Society (ACS)

SP - 4532-4535

IS - 17

VL - 16

PMID - 25115452

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2014_Lvov,

author = {Andrey Lvov and Valerii Z. Shirinian and Vadim V. Kachala and Alexey M Kavun and Igor V. Zavarzin and Mikhail M. Krayushkin},

title = {Photoinduced Skeletal Rearrangement of Diarylethenes Comprising Oxazole and Phenyl Rings},

journal = {Organic Letters},

year = {2014},

volume = {16},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://doi.org/10.1021/ol502073t},

number = {17},

pages = {4532--4535},

doi = {10.1021/ol502073t}

}

MLA

Cite this

MLA Copy

Lvov, Andrey, et al. “Photoinduced Skeletal Rearrangement of Diarylethenes Comprising Oxazole and Phenyl Rings.” Organic Letters, vol. 16, no. 17, Aug. 2014, pp. 4532-4535. https://doi.org/10.1021/ol502073t.