The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-Cyclization and 1,3-dipolar cycloaddition
Publication type: Journal Article
Publication date: 2005-11-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Abstract The reaction of Schiff bases with fluorocarbene, generated by reduction of dibromofluoromethane with active lead in the presence of Bu 4 NBr under ultrasound irradiation, involves the formation of fluoro-substituted azomethine ylides which undergo cyclization into aziridines. 1,3-Cyclization of ylides, generated from N -arylimines of benzaldehyde, proceeds stereoselectively. When carrying out the reaction of Schiff bases with fluorocarbene in the presence of dimethyl maleate or dimethyl acetylenedicarboxylate, the products of dehydrofluorination of the primary adducts of the 1,3-dipolar cycloaddition of fluoro-substituted azomethine ylides to multiple bonds of dipolarophiles were obtained. In the case of the reaction of N -alkylimines of benzaldehyde the cycloaddition of ylides to dimethyl maleate completely suppressed the cyclization to aziridines.
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Konev A. S., Novikov M. S., Khlebnikov A. F. The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-Cyclization and 1,3-dipolar cycloaddition // Tetrahedron Letters. 2005. Vol. 46. No. 48. pp. 8337-8340.
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Konev A. S., Novikov M. S., Khlebnikov A. F. The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-Cyclization and 1,3-dipolar cycloaddition // Tetrahedron Letters. 2005. Vol. 46. No. 48. pp. 8337-8340.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tetlet.2005.09.165
UR - https://doi.org/10.1016/j.tetlet.2005.09.165
TI - The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-Cyclization and 1,3-dipolar cycloaddition
T2 - Tetrahedron Letters
AU - Konev, Alexander S.
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2005
DA - 2005/11/01
PB - Elsevier
SP - 8337-8340
IS - 48
VL - 46
SN - 0040-4039
SN - 1873-3581
ER -
Cite this
BibTex (up to 50 authors)
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@article{2005_Konev,
author = {Alexander S. Konev and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-Cyclization and 1,3-dipolar cycloaddition},
journal = {Tetrahedron Letters},
year = {2005},
volume = {46},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/j.tetlet.2005.09.165},
number = {48},
pages = {8337--8340},
doi = {10.1016/j.tetlet.2005.09.165}
}
Cite this
MLA
Copy
Konev, Alexander S., et al. “The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-Cyclization and 1,3-dipolar cycloaddition.” Tetrahedron Letters, vol. 46, no. 48, Nov. 2005, pp. 8337-8340. https://doi.org/10.1016/j.tetlet.2005.09.165.