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Heterolytic fragmentation of 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydro-quinuclidine-2,3-dicarboxylic acid esters

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
, 
Lev Oganovich Atovmyan 2
Lev Oganovich Atovmyan
, 
Arvi Rauk 3
Arvi Rauk
10.1070/MC1996v006n03ABEH000602
Published 1996-06-30
Communication , Volume 6, Issue 3, 108-110
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Kostyanovsky R. G. et al. Heterolytic fragmentation of 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydro-quinuclidine-2,3-dicarboxylic acid esters // Mendeleev Communications. 1996. Vol. 6. No. 3. pp. 108-110.
GOST all authors (up to 50) Copy
Kostyanovsky R. G., Èl'natanov Y. I., Chervin I. I., Konovalikhin S. V., Atovmyan L. O., Rauk A. Heterolytic fragmentation of 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydro-quinuclidine-2,3-dicarboxylic acid esters // Mendeleev Communications. 1996. Vol. 6. No. 3. pp. 108-110.
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TY - JOUR
DO - 10.1070/MC1996v006n03ABEH000602
UR - https://mendcomm.colab.ws/publications/10.1070/MC1996v006n03ABEH000602
TI - Heterolytic fragmentation of 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydro-quinuclidine-2,3-dicarboxylic acid esters
T2 - Mendeleev Communications
AU - Kostyanovsky, Remir Grigorevich
AU - Èl'natanov, Yuri Il'ich
AU - Chervin, Ivan Ivanovich
AU - Konovalikhin, Sergei Vladimirovich
AU - Atovmyan, Lev Oganovich
AU - Rauk, Arvi
PY - 1996
DA - 1996/06/30
PB - Mendeleev Communications
SP - 108-110
IS - 3
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 Lev Oganovich Atovmyan and Arvi Rauk},
title = {Heterolytic fragmentation of 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydro-quinuclidine-2,3-dicarboxylic acid esters},
journal = {Mendeleev Communications},
year = {1996},
volume = {6},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1996v006n03ABEH000602},
number = {3},
pages = {108--110},
doi = {10.1070/MC1996v006n03ABEH000602}
}
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Kostyanovsky, Remir Grigorevich, et al. “Heterolytic fragmentation of 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydro-quinuclidine-2,3-dicarboxylic acid esters.” Mendeleev Communications, vol. 6, no. 3, Jun. 1996, pp. 108-110. https://mendcomm.colab.ws/publications/10.1070/MC1996v006n03ABEH000602.

Abstract

The title quinuclidines undergo cleavage under the action of acids or H2O to give Δ2-dehydro-4-piperidones 4, 5 and isobutylene; the resulting redistribution of bond lengths upon N-protonation has been demonstated by X-ray diffraction methods for picrate 2a as well as by ab initio calculations for quinuclidine la, cation 2a’ and zwitterion 2a”, the latter being the most suitable as an intermediate of the fragmentation.

References

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R. G. Kostyanovsky, Yu. I. El’natanov, I. I. Chervin, S. V. Konovalikhin, A. B. Zolotoi and L. O. Atovmyan, Mendeleev Coinmun., in press.
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