Russian Journal of Organic Chemistry

, volume 38 , issue 5 , pages 672-682

1,3-Dipolar cycloaddition of azomethine ylides generated from Schiff bases and difluorocarbene to symmetric olefins

M.S. Novikov ¹

A F Khlebnikov ¹

E S Sidorina ¹

A E Masalev ¹

J. Kopf ²

R R Kostikov ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

St. Petersburg state University, St. Petersburg, Russia |

Institut für anorganische Chemie, Hamburg, Germany |

Publication type: Journal Article

Publication date: 2002-01-01

Pleiades Publishing

Russian Journal of Organic Chemistry

scimago Q4

wos Q4

SJR: 0.190

CiteScore: 1.3

Impact factor: 0.9

ISSN: 10704280, 16083393

DOI: 10.1023/A:1019659021891

Copy DOI

Organic Chemistry

Abstract

Difluoro(iminio)methanides generated by the action of difluorocarbene on Schiff bases react with derivatives of maleic and fumaric acids, following the 1,3-dipolar cycloaddition pattern to give 2,2-difluoropyrrolidines which were detected by gas chromatography-mass spectrometry. The final products are stereo-isomeric substituted 2-pyrrolidinones formed by hydrolysis of difluoropyrrolidines and their dehydrofluorination products, 2-fluoro-4,5-dihydropyrroles. The observed stereoselectivity of the cycloaddition suggests Z configuration of intermediate ylide and both endo- and exo-approach to the dipolarophile in the transition state corresponding to cycloaddition.

Found

5 citations

Novikov Mikhail

DSc in Chemistry, associate professor

216 publications, 4 151 citations, 54 reviews

h-index: 33

Saint Petersburg State University

Top-30

Journals

	1 2 3 4
Russian Journal of Organic Chemistry	Russian Journal of Organic Chemistry, 4, 50% Russian Journal of Organic Chemistry 4 publications, 50%
Tetrahedron Letters	Tetrahedron Letters, 1, 12.5% Tetrahedron Letters 1 publication, 12.5%
Crystals	Crystals, 1, 12.5% Crystals 1 publication, 12.5%
ChemInform	ChemInform, 1, 12.5% ChemInform 1 publication, 12.5%
Journal of Organic Chemistry	Journal of Organic Chemistry, 1, 12.5% Journal of Organic Chemistry 1 publication, 12.5%
	1 2 3 4

Publishers

	1 2 3 4
Pleiades Publishing	Pleiades Publishing, 4, 50% Pleiades Publishing 4 publications, 50%
Elsevier	Elsevier, 1, 12.5% Elsevier 1 publication, 12.5%
MDPI	MDPI, 1, 12.5% MDPI 1 publication, 12.5%
Wiley	Wiley, 1, 12.5% Wiley 1 publication, 12.5%
American Chemical Society (ACS)	American Chemical Society (ACS), 1, 12.5% American Chemical Society (ACS) 1 publication, 12.5%
	1 2 3 4

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

Novikov M. et al. 1,3-Dipolar cycloaddition of azomethine ylides generated from Schiff bases and difluorocarbene to symmetric olefins // Russian Journal of Organic Chemistry. 2002. Vol. 38. No. 5. pp. 672-682.

GOST all authors (up to 50) Copy

Novikov M., Khlebnikov A. F., Sidorina E. S., Masalev A. E., Kopf J., Kostikov R. R. 1,3-Dipolar cycloaddition of azomethine ylides generated from Schiff bases and difluorocarbene to symmetric olefins // Russian Journal of Organic Chemistry. 2002. Vol. 38. No. 5. pp. 672-682.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1023/A:1019659021891

UR - https://doi.org/10.1023/A:1019659021891

TI - 1,3-Dipolar cycloaddition of azomethine ylides generated from Schiff bases and difluorocarbene to symmetric olefins

T2 - Russian Journal of Organic Chemistry

AU - Novikov, M.S.

AU - Khlebnikov, A F

AU - Sidorina, E S

AU - Masalev, A E

AU - Kopf, J.

AU - Kostikov, R R

PY - 2002

DA - 2002/01/01

PB - Pleiades Publishing

SP - 672-682

IS - 5

VL - 38

SN - 1070-4280

SN - 1608-3393

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2002_Novikov,

author = {M.S. Novikov and A F Khlebnikov and E S Sidorina and A E Masalev and J. Kopf and R R Kostikov},

title = {1,3-Dipolar cycloaddition of azomethine ylides generated from Schiff bases and difluorocarbene to symmetric olefins},

journal = {Russian Journal of Organic Chemistry},

year = {2002},

volume = {38},

publisher = {Pleiades Publishing},

month = {jan},

url = {https://doi.org/10.1023/A:1019659021891},

number = {5},

pages = {672--682},

doi = {10.1023/A:1019659021891}

}

MLA

Cite this

MLA Copy

Novikov, M.S., et al. “1,3-Dipolar cycloaddition of azomethine ylides generated from Schiff bases and difluorocarbene to symmetric olefins.” Russian Journal of Organic Chemistry, vol. 38, no. 5, Jan. 2002, pp. 672-682. https://doi.org/10.1023/A:1019659021891.