Russian Journal of Organic Chemistry

, том 38 , издание 5 , страницы 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

Скрыть аффилиации авторов Показать аффилиации авторов: 2 аффилиации

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

Institut für anorganische Chemie, Hamburg, Germany |

Тип публикации: Journal Article

Дата публикации: 2002-01-01

Pleiades Publishing

Russian Journal of Organic Chemistry

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wos Q4

БС3

SJR: 0.190

CiteScore: 1.3

Impact factor: 0.9

ISSN: 10704280, 16083393

DOI: 10.1023/A:1019659021891

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Organic Chemistry

Краткое описание

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.

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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.

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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.

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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 -

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@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}

}

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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.