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1,5-Sigmatropic Shifts of Chlorine in the Cyclopentadiene Ring

Igor Evguen'evich Mikhailov 1
Igor Evguen'evich Mikhailov
, 
Galina Anatol'evna Dushenko 1
Galina Anatol'evna Dushenko
, 
Alexander Vadimovich Kisin 2
Alexander Vadimovich Kisin
, 
Clemens Muegge 3
Clemens Muegge
, 
Adolf Zschunke 4
Adolf Zschunke
, 
Vladimir Isaakovich Minkin 1
Vladimir Isaakovich Minkin
10.1070/MC1994v004n03ABEH000358
Published 1994-06-30
Communication , Volume 4, Issue 3, 85-88
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Mikhailov I. E. et al. 1,5-Sigmatropic Shifts of Chlorine in the Cyclopentadiene Ring // Mendeleev Communications. 1994. Vol. 4. No. 3. pp. 85-88.
GOST all authors (up to 50) Copy
Mikhailov I. E., Dushenko G. A., Kisin A. V., Muegge C., Zschunke A., Minkin V. I. 1,5-Sigmatropic Shifts of Chlorine in the Cyclopentadiene Ring // Mendeleev Communications. 1994. Vol. 4. No. 3. pp. 85-88.
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TY - JOUR
DO - 10.1070/MC1994v004n03ABEH000358
UR - https://mendcomm.colab.ws/publications/10.1070/MC1994v004n03ABEH000358
TI - 1,5-Sigmatropic Shifts of Chlorine in the Cyclopentadiene Ring
T2 - Mendeleev Communications
AU - Mikhailov, Igor Evguen'evich
AU - Dushenko, Galina Anatol'evna
AU - Kisin, Alexander Vadimovich
AU - Muegge, Clemens
AU - Zschunke, Adolf
AU - Minkin, Vladimir Isaakovich
PY - 1994
DA - 1994/06/30
PB - Mendeleev Communications
SP - 85-88
IS - 3
VL - 4
ER -
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@article{1994_Mikhailov,
author = {Igor Evguen'evich Mikhailov and Galina Anatol'evna Dushenko and Alexander Vadimovich Kisin and Clemens Muegge and Adolf Zschunke and Vladimir Isaakovich Minkin},
title = {1,5-Sigmatropic Shifts of Chlorine in the Cyclopentadiene Ring},
journal = {Mendeleev Communications},
year = {1994},
volume = {4},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1994v004n03ABEH000358},
number = {3},
pages = {85--88},
doi = {10.1070/MC1994v004n03ABEH000358}
}
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Mikhailov, Igor Evguen'evich, et al. “1,5-Sigmatropic Shifts of Chlorine in the Cyclopentadiene Ring.” Mendeleev Communications, vol. 4, no. 3, Jun. 1994, pp. 85-88. https://mendcomm.colab.ws/publications/10.1070/MC1994v004n03ABEH000358.

Abstract

Intramolecular rearrangement due to successive 1,5-sigmatropic shifts of chlorine over a five-membered ring were found to occur in 5-chloro-1-alky1-2,3,4,5-tetramethoxycarbonylcyclopentadienes with energy barriers to chlorine migration falling in the range 26.0–27.3 kcal mol–1.

References

1.
1,5‐Sigmatropic shifts of bromine over a cyclopentadiene ring
Minkin V.I., Mikhailov I.E., Dushenko G.A., Yudilevich J.A., Minyaev R.M., Zschunke A., Mögge K.
Journal of Physical Organic Chemistry, 1991
2.
10.1070/MC1994v004n03ABEH000358_bib2
Mikhailov
Zh. Org. Khim., 1988
3.
Rapid nucleophilic substitutions on cyclopentadienyl iodide and bromide
Breslow R., Canary J.W.
Journal of the American Chemical Society, 1991
4.
Mikhailov I.E., Dushenko G.A., Kamenetskaya I.A., Kompan O.E., Struchkov Y.T., Minkin V.I.
Mendeleev Communications, 1991
5.
10.1070/MC1994v004n03ABEH000358_bib5
Hansen
1981