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Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydroquinuclidine-2,3-di-carboxylate

Remir Grigorevich Kostyanovsky 1
Remir Grigorevich Kostyanovsky
, 
Yuri Il'ich Èl'natanov 1
Yuri Il'ich Èl'natanov
, 
Ivan Ivanovich Chervin 1
Ivan Ivanovich Chervin
, 
Sergei Vladimirovich Konovalikhin 2
Sergei Vladimirovich Konovalikhin
, 
Alexander Borokhovich Zolotoi 2
Alexander Borokhovich Zolotoi
, 
Lev Oganovich Atovmyan 2
Lev Oganovich Atovmyan
10.1070/MC1996v006n04ABEH000619
Published 1996-08-31
Communication , Volume 6, Issue 4, 143-145
6
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Kostyanovsky R. G. et al. Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydroquinuclidine-2,3-di-carboxylate // Mendeleev Communications. 1996. Vol. 6. No. 4. pp. 143-145.
GOST all authors (up to 50) Copy
Kostyanovsky R. G., Èl'natanov Y. I., Chervin I. I., Konovalikhin S. V., Zolotoi A. B., Atovmyan L. O. Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydroquinuclidine-2,3-di-carboxylate // Mendeleev Communications. 1996. Vol. 6. No. 4. pp. 143-145.
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TY - JOUR
DO - 10.1070/MC1996v006n04ABEH000619
UR - https://mendcomm.colab.ws/publications/10.1070/MC1996v006n04ABEH000619
TI - Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydroquinuclidine-2,3-di-carboxylate
T2 - Mendeleev Communications
AU - Kostyanovsky, Remir Grigorevich
AU - Èl'natanov, Yuri Il'ich
AU - Chervin, Ivan Ivanovich
AU - Konovalikhin, Sergei Vladimirovich
AU - Zolotoi, Alexander Borokhovich
AU - Atovmyan, Lev Oganovich
PY - 1996
DA - 1996/08/31
PB - Mendeleev Communications
SP - 143-145
IS - 4
VL - 6
ER -
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@article{1996_Kostyanovsky,
author = {Remir Grigorevich Kostyanovsky and Yuri Il'ich Èl'natanov and Ivan Ivanovich Chervin and Sergei Vladimirovich Konovalikhin and Alexander Borokhovich Zolotoi and Lev Oganovich Atovmyan},
title = {Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydroquinuclidine-2,3-di-carboxylate},
journal = {Mendeleev Communications},
year = {1996},
volume = {6},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1996v006n04ABEH000619},
number = {4},
pages = {143--145},
doi = {10.1070/MC1996v006n04ABEH000619}
}
MLA
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Kostyanovsky, Remir Grigorevich, et al. “Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydroquinuclidine-2,3-di-carboxylate.” Mendeleev Communications, vol. 6, no. 4, Aug. 1996, pp. 143-145. https://mendcomm.colab.ws/publications/10.1070/MC1996v006n04ABEH000619.

Abstract

Triacetonamine reacts with dimethyl acetylenedicarboxylate in MeOH to give an ordinary adduct, aminomaleate 2, while in aprotic solvents quinuclidine 1 is formed under mild conditions and in high yield; its structure is confirmed by spectroscopic methods as well as X-ray diffraction analysis. A mechanism of autoassembling is proposed, and chemical transformations of 1 with retention of quinuclidine nucleus are studied.

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