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New calix[4]resorcinol rccc diastereoisomer with terminal triple bonds: Synthesis, structural features and reactions

Irina Rafaelevna Mironova (Knyazeva) 1
Irina Rafaelevna Mironova (Knyazeva)
, 
Victor Vasil'evich Syakaev 1
Victor Vasil'evich Syakaev
, 
Wolf D Habicher 2
Wolf D Habicher
, 
Alexander Romanovich Burilov 1
Alexander Romanovich Burilov
1 A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
2 Institute of Organic Chemistry, Dresden University of Technology, Dresden, Germany
10.1016/j.mencom.2023.04.031
Published 2023-04-13
Communication , Volume 33, Issue 3, 397-400
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Mironova (Knyazeva) I. R. et al. New calix[4]resorcinol rccc diastereoisomer with terminal triple bonds: Synthesis, structural features and reactions // Mendeleev Communications. 2023. Vol. 33. No. 3. pp. 397-400.
GOST all authors (up to 50) Copy
Mironova (Knyazeva) I. R., Syakaev V. V., Habicher W. D., Burilov A. R. New calix[4]resorcinol rccc diastereoisomer with terminal triple bonds: Synthesis, structural features and reactions // Mendeleev Communications. 2023. Vol. 33. No. 3. pp. 397-400.
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TY - JOUR
DO - 10.1016/j.mencom.2023.04.031
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.04.031
TI - New calix[4]resorcinol rccc diastereoisomer with terminal triple bonds: Synthesis, structural features and reactions
T2 - Mendeleev Communications
AU - Mironova (Knyazeva), Irina Rafaelevna
AU - Syakaev, Victor Vasil'evich
AU - Habicher, Wolf D
AU - Burilov, Alexander Romanovich
PY - 2023
DA - 2023/04/13
PB - Mendeleev Communications
SP - 397-400
IS - 3
VL - 33
ER -
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@article{2023_Mironova (Knyazeva),
author = {Irina Rafaelevna Mironova (Knyazeva) and Victor Vasil'evich Syakaev and Wolf D Habicher and Alexander Romanovich Burilov},
title = {New calix[4]resorcinol rccc diastereoisomer with terminal triple bonds: Synthesis, structural features and reactions},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.04.031},
number = {3},
pages = {397--400},
doi = {10.1016/j.mencom.2023.04.031}
}
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Mironova (Knyazeva), Irina Rafaelevna, et al. “New calix[4]resorcinol rccc diastereoisomer with terminal triple bonds: Synthesis, structural features and reactions.” Mendeleev Communications, vol. 33, no. 3, Apr. 2023, pp. 397-400. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.04.031.

Keywords

1
2
3-triazoles.
calixresorcinols
click reaction
condensation
conformation
diastereoisomers

Abstract

One-pot acid-catalyzed cyclocondensation of 2-methyl-resorcinol with 4-(propargyloxy)benzaldehyde in CHCl3/CF3CO2H media affords all-cis (rccc) and/or cis-trans-trans (rctt) calix[4]resorcinol diastereomers bearing four terminal alkyne groups at aromatic substituents, the isomer ratio and yield being dependent on the CHCl3/CF3CO2H ratio. The rctt isomer (kinetic control product) can be converted to thermodynamically more stable rccc isomer at prolonged refluxing in CHCl3/CF3CO2H mixture. The rccc diastereomer was subjected to additional propargylation followed by the click reactions with benzylic azides to afford new highly triazolated calix[4]resorcinols.

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