1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins

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1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins. / Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R.

In: Russian Journal of Organic Chemistry, Vol. 38, No. 11, 2002, p. 1647-1654.

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

BibTeX

@article{32bdcd2f72d048f28b5ddff8889dab4c,

title = "1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins",

abstract = "Iminiodifluoromethanides generated from difluorocarbene and benzophenone or fluorenone imines enter into reaction of 1,3-cycloaddition with electron-deficient alkenes to furnish pyrrolidone derivatives. The generation of iminiodifluoromethanides from alkyl N-benzhydrylidene glycinates in the presence of dipolarophiles is liable to complication by a concurrent proton shift in the initial imine giving NH-azomethine ylide also capable of 1,3-dipolar cycloaddition resulting in a side product of pyrrolidone series. The use of active lead instead of lead powder as reductant for dibromodifluoromethane in generation of difluorocarbene permits suppressing formation of the side products in these reactions.",

author = "Novikov, {M. S.} and Khlebnikov, {A. F.} and Kostikov, {R. R.}",

note = "Funding Information: * The study was financially supported by the Russian Founda-tion for Basic Research (grant no. 02-03-32735a) and by Ministry of Education of the Russian Federation (grant no. E00-5.0-371).",

year = "2002",

doi = "10.1023/A:1022518319349",

language = "English",

volume = "38",

pages = "1647--1654",

journal = "Russian Journal of Organic Chemistry",

issn = "1070-4280",

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

number = "11",

}

RIS

TY - JOUR

T1 - 1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins

AU - Novikov, M. S.

AU - Khlebnikov, A. F.

AU - Kostikov, R. R.

N1 - Funding Information: * The study was financially supported by the Russian Founda-tion for Basic Research (grant no. 02-03-32735a) and by Ministry of Education of the Russian Federation (grant no. E00-5.0-371).

PY - 2002

Y1 - 2002

N2 - Iminiodifluoromethanides generated from difluorocarbene and benzophenone or fluorenone imines enter into reaction of 1,3-cycloaddition with electron-deficient alkenes to furnish pyrrolidone derivatives. The generation of iminiodifluoromethanides from alkyl N-benzhydrylidene glycinates in the presence of dipolarophiles is liable to complication by a concurrent proton shift in the initial imine giving NH-azomethine ylide also capable of 1,3-dipolar cycloaddition resulting in a side product of pyrrolidone series. The use of active lead instead of lead powder as reductant for dibromodifluoromethane in generation of difluorocarbene permits suppressing formation of the side products in these reactions.

AB - Iminiodifluoromethanides generated from difluorocarbene and benzophenone or fluorenone imines enter into reaction of 1,3-cycloaddition with electron-deficient alkenes to furnish pyrrolidone derivatives. The generation of iminiodifluoromethanides from alkyl N-benzhydrylidene glycinates in the presence of dipolarophiles is liable to complication by a concurrent proton shift in the initial imine giving NH-azomethine ylide also capable of 1,3-dipolar cycloaddition resulting in a side product of pyrrolidone series. The use of active lead instead of lead powder as reductant for dibromodifluoromethane in generation of difluorocarbene permits suppressing formation of the side products in these reactions.

UR - http://www.scopus.com/inward/record.url?scp=0036922287&partnerID=8YFLogxK

U2 - 10.1023/A:1022518319349

DO - 10.1023/A:1022518319349

M3 - Article

AN - SCOPUS:0036922287

VL - 38

SP - 1647

EP - 1654

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 11

ER -

ID: 99351729