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

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1,3-Dipolar cycloaddition of azomethine ylides generated from Schiff bases and difluorocarbene to symmetric olefins. / Novikov, M. S.; Khlebnikov, A. F.; Sidorina, E. S.; Masalev, A. E.; Kopf, J.; Kostikov, R. R.

In: Russian Journal of Organic Chemistry, Vol. 38, No. 5, 2002, p. 672-682.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{54f9710f3ffd433594586893994779fa,

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

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 stereoisomeric 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.",

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

note = "Funding Information: This study was financially supported by the Russian Foundation for Basic Research (project no. 99-03-32 930a) and by the Ministry of Education of the Russian Federation (project no. E00-5.0-371).",

year = "2002",

doi = "10.1023/A:1019659021891",

language = "English",

volume = "38",

pages = "672--682",

journal = "Russian Journal of Organic Chemistry",

issn = "1070-4280",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "5",

}

RIS

TY - JOUR

T1 - 1,3-Dipolar cycloaddition of azomethine ylides generated from Schiff bases and difluorocarbene to symmetric olefins

AU - Novikov, M. S.

AU - Khlebnikov, A. F.

AU - Sidorina, E. S.

AU - Masalev, A. E.

AU - Kopf, J.

AU - Kostikov, R. R.

N1 - Funding Information: This study was financially supported by the Russian Foundation for Basic Research (project no. 99-03-32 930a) and by the Ministry of Education of the Russian Federation (project no. E00-5.0-371).

PY - 2002

Y1 - 2002

N2 - 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 stereoisomeric 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.

AB - 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 stereoisomeric 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.

UR - http://www.scopus.com/inward/record.url?scp=0036343910&partnerID=8YFLogxK

U2 - 10.1023/A:1019659021891

DO - 10.1023/A:1019659021891

M3 - Article

AN - SCOPUS:0036343910

VL - 38

SP - 672

EP - 682

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 5

ER -

ID: 99351847