Rh2 (OAc)4 -catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters
Publication type: Journal Article
Publication date: 2017-08-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters proceeds through an intermediate generation of azirinium ylide suffering a nonstereoselective ring opening to form (3Z)- and (3E)-2-azahexa-1,3,5-trienes. The former depending on configuration of the C5=C6 bond may undergo cyclization either in derivative of 2,3-dihydropyridine, or in pyrrolium ylide that isomerizes into a derivative of 1H-pyrrole. According to DFT calculation, the preferred formation of pyrroles at increasing volume of Z-substituent at the atom C6 and of substituents at the atom C1 of 2-azahexatriene occurs due to the destabilization of more sterically loaded transition states of 1,6-cyclization.
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8
Total citations:
8
Citations from 2024:
2
(25%)
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GOST
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Zavyalov K. V. et al. Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters // Russian Journal of Organic Chemistry. 2017. Vol. 53. No. 8. pp. 1214-1221.
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Zavyalov K. V., Novikov M., Khlebnikov А. F., Rostovskii N. V., Starova G. L. Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters // Russian Journal of Organic Chemistry. 2017. Vol. 53. No. 8. pp. 1214-1221.
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RIS
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TY - JOUR
DO - 10.1134/S1070428017080097
UR - https://doi.org/10.1134/S1070428017080097
TI - Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters
T2 - Russian Journal of Organic Chemistry
AU - Zavyalov, K V
AU - Novikov, M.S.
AU - Khlebnikov, А F
AU - Rostovskii, N V
AU - Starova, G L
PY - 2017
DA - 2017/08/01
PB - Pleiades Publishing
SP - 1214-1221
IS - 8
VL - 53
SN - 1070-4280
SN - 1608-3393
ER -
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BibTex (up to 50 authors)
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@article{2017_Zavyalov,
author = {K V Zavyalov and M.S. Novikov and А F Khlebnikov and N V Rostovskii and G L Starova},
title = {Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters},
journal = {Russian Journal of Organic Chemistry},
year = {2017},
volume = {53},
publisher = {Pleiades Publishing},
month = {aug},
url = {https://doi.org/10.1134/S1070428017080097},
number = {8},
pages = {1214--1221},
doi = {10.1134/S1070428017080097}
}
Cite this
MLA
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Zavyalov, K. V., et al. “Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters.” Russian Journal of Organic Chemistry, vol. 53, no. 8, Aug. 2017, pp. 1214-1221. https://doi.org/10.1134/S1070428017080097.