1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins
Publication type: Journal Article
Publication date: 2002-01-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
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.
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Novikov M., Khlebnikov A. F., Kostikov R. R. 1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins // Russian Journal of Organic Chemistry. 2002. Vol. 38. No. 11. pp. 1647-1654.
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Novikov M., Khlebnikov A. F., Kostikov R. R. 1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins // Russian Journal of Organic Chemistry. 2002. Vol. 38. No. 11. pp. 1647-1654.
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TY - JOUR
DO - 10.1023/A:1022518319349
UR - https://doi.org/10.1023/A:1022518319349
TI - 1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins
T2 - Russian Journal of Organic Chemistry
AU - Novikov, M.S.
AU - Khlebnikov, A F
AU - Kostikov, R R
PY - 2002
DA - 2002/01/01
PB - Pleiades Publishing
SP - 1647-1654
IS - 11
VL - 38
SN - 1070-4280
SN - 1608-3393
ER -
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BibTex (up to 50 authors)
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@article{2002_Novikov,
author = {M.S. Novikov and A F Khlebnikov and R R Kostikov},
title = {1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins},
journal = {Russian Journal of Organic Chemistry},
year = {2002},
volume = {38},
publisher = {Pleiades Publishing},
month = {jan},
url = {https://doi.org/10.1023/A:1022518319349},
number = {11},
pages = {1647--1654},
doi = {10.1023/A:1022518319349}
}
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MLA
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Novikov, M.S., et al. “1,3-Dipolar cycloaddition of azomethine ylides generated from ketimines and difluorocarbene to symmetrically substituted olefins.” Russian Journal of Organic Chemistry, vol. 38, no. 11, Jan. 2002, pp. 1647-1654. https://doi.org/10.1023/A:1022518319349.
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