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Aza-Favorsky reaction with regioisomeric C- and N-linked 1,4-bis(imino)benzenes: Synthetic and reactivity dissimilarities

Elena Yur'evna Schmidt 1
Elena Yur'evna Schmidt
, 
Nadezhda Victorovna Semenova 1
Nadezhda Victorovna Semenova
, 
Ivan A. Bidusenko 1
Ivan A. Bidusenko
, 
Nadezhda Il'inichna Protsuk 1
Nadezhda Il'inichna Protsuk
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2023.09.017
Published 2023-09-01
Communication , Volume 33, Issue 5, 642-644
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Schmidt E. Y. 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.
GOST all authors (up to 50) Copy
Schmidt E. Y., 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://mendcomm.colab.ws/publications/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 Yur'evna
AU - Semenova, Nadezhda Victorovna
AU - Bidusenko, Ivan A.
AU - Protsuk, Nadezhda Il'inichna
AU - Ushakov, Igor Alekseevich
AU - Trofimov, Boris Aleksandrovich
PY - 2023
DA - 2023/09/01
PB - Mendeleev Communications
SP - 642-644
IS - 5
VL - 33
ER -
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@article{2023_Schmidt,
author = {Elena Yur'evna Schmidt and Nadezhda Victorovna Semenova and Ivan A. Bidusenko and Nadezhda Il'inichna Protsuk and Igor Alekseevich Ushakov and Boris Aleksandrovich 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 = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.017},
number = {5},
pages = {642--644},
doi = {10.1016/j.mencom.2023.09.017}
}
MLA
Cite this
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Schmidt, Elena Yur'evna, 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://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.017.

Keywords

acetylenes
diamines
ethynylation.
imines
propargylic amines
superbases

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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