Aza-Favorsky reaction with regioisomeric C- and N-linked 1,4-bis(imino)benzenes: Synthetic and reactivity dissimilarities
Publication type: Journal Article
Publication date: 2023-09-01
scimago Q3
wos Q3
SJR: 0.305
CiteScore: 3.0
Impact factor: 1.7
ISSN: 09599436, 1364551X
General Chemistry
Abstract
Structurally analogous C- and N-linked 1,4-bis(imino)-functionalized benzenes react with acetylenes in the KOBut/ DMSO superbase system to give the corresponding bis-(propargylamino)-containing derivatives in 62–82% yields (C-linking) or 38–42% yields (N-linking). In the latter case, with phenylacetylene, the yields of mono- and bisadducts were 32 and 38%, respectively. The observed dissimilarities between both bisimine chemotypes in the reactivity and synthetic outcomes imply the long-range adverse repulsive interaction between nitrogen anionic center and the second nitrogen atom in the N-linked 1,4-bis(imino) benzenes.
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Schmidt E. Yu. et al. Aza-Favorsky reaction with regioisomeric C- and N-linked 1,4-bis(imino)benzenes: Synthetic and reactivity dissimilarities // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 642-644.
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Schmidt E. Yu., Semenova N. V., Bidusenko I. A., Protsuk N. I., Ushakov I. A., Trofimov B. A. Aza-Favorsky reaction with regioisomeric C- and N-linked 1,4-bis(imino)benzenes: Synthetic and reactivity dissimilarities // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 642-644.
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TY - JOUR
DO - 10.1016/j.mencom.2023.09.017
UR - https://doi.org/10.1016/j.mencom.2023.09.017
TI - Aza-Favorsky reaction with regioisomeric C- and N-linked 1,4-bis(imino)benzenes: Synthetic and reactivity dissimilarities
T2 - Mendeleev Communications
AU - Schmidt, Elena Yu
AU - Semenova, Nadezhda V
AU - Bidusenko, Ivan A
AU - Protsuk, Nadezhda I
AU - Ushakov, I A
AU - Trofimov, Boris A.
PY - 2023
DA - 2023/09/01
PB - OOO Zhurnal "Mendeleevskie Soobshcheniya"
SP - 642-644
IS - 5
VL - 33
SN - 0959-9436
SN - 1364-551X
ER -
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@article{2023_Schmidt,
author = {Elena Yu Schmidt and Nadezhda V Semenova and Ivan A Bidusenko and Nadezhda I Protsuk and I A Ushakov and Boris A. Trofimov},
title = {Aza-Favorsky reaction with regioisomeric C- and N-linked 1,4-bis(imino)benzenes: Synthetic and reactivity dissimilarities},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {OOO Zhurnal "Mendeleevskie Soobshcheniya"},
month = {sep},
url = {https://doi.org/10.1016/j.mencom.2023.09.017},
number = {5},
pages = {642--644},
doi = {10.1016/j.mencom.2023.09.017}
}
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MLA
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Schmidt, Elena Yu., et al. “Aza-Favorsky reaction with regioisomeric C- and N-linked 1,4-bis(imino)benzenes: Synthetic and reactivity dissimilarities.” Mendeleev Communications, vol. 33, no. 5, Sep. 2023, pp. 642-644. https://doi.org/10.1016/j.mencom.2023.09.017.