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.
Document Type:
Article
Language: English
Citation:
I. E. Mikhailov, G. A. Dushenko, A. V. Kisin, C. Muegge, A. Zschunke, V. I. Minkin, “1,5-Sigmatropic Shifts of Chlorine in the Cyclopentadiene Ring”, Mendeleev Commun., 4:3 (1994), 85–88
Linking options:
https://www.mathnet.ru/eng/mendc5162
https://www.mathnet.ru/eng/mendc/v4/i3/p85
This publication is cited in the following 10 articles:
I. E. Mikhailov, G. A. Dushenko, V. I. Minkin, “Pentacarboxycyclopentadienes in Organic Synthesis”, Russ J Org Chem, 57:11 (2021), 1757
G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “3,3-Sigmatropic Shifts of Allyl Group Along Cyclopentadiene Ring Perimeter”, Russ J Gen Chem, 90:2 (2020), 161
G.A. Dushenko, I.E. Mikhailov, O.I. Mikhailova, R.M. Minyaev, V.I. Minkin, “STROENIE I?FLUKTUIRUYuSchEE POVEDENIE PENTAMETOKSIKARBONILTsIKLOPENTADIENA, “Doklady Akademii nauk””, Doklady Akademii Nauk, 2017, no. 6, 648
G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “Structure and fluxional behavior of pentamethoxycarbonylcyclopentadiene”, Dokl Chem, 476:2 (2017), 230
G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “Mechanisms of circumambulatory rearrangements of 5-halogeno-1,2,3,4,5-pentamethoxycarbonylcyclopentadienes”, Russ Chem Bull, 64:9 (2015), 2043
Sergei M. Lukyanov, Alla V. Koblik, Patai's Chemistry of Functional Groups, 2009
Do Hyong Kim, James A. Mulholland, Jae-Yong Ryu, “Formation of polychlorinated naphthalenes from chlorophenols”, Proceedings of the Combustion Institute, 30:1 (2005), 1245
A. A. Bumber, G. A. Dushenko, I. A. Profatilova, A. A. Arutyunyants, I. E. Mikhailov, “Electrochemical conversions of pentaphenyl(methoxycarbonyl)cyclopentadiene derivatives”, Russ J Electrochem, 36:5 (2000), 553
Vladimir I. Minkin, Ruslan M. Minyaev, Igor V. Dorogan, “Computational modeling of the mechanisms of circumambulatory rearrangements of main-group migrants in the cyclopropene ring”, Journal of Molecular Structure: THEOCHEM, 398-399 (1997), 237
Rainer Koch, Ming Wah Wong, Curt Wentrup, “Facile 1,3- and 1,5-Chlorine Migration”, J. Org. Chem., 61:20 (1996), 6809