Abstract:
In 7-(1,2,3,4,5,6,7-heptaphenylcycloheptatrienyl) isothiocyanate and isoselenocyanate, migration of isothiocyanate and isoselenocyanate groups along the perimeter of the seven-membered ring occurs via an intramolecular dissociation–recombination mechanism with high free energy barriers (ΔG298≠) of 24.3 and 22.4 kcal mol–1, respectively.
Document Type:
Article
Language: English
Citation:
G. A. Dushenko, I. E. Mikhailov, A. Zschunke, G. Reck, B. Schulz, V. I. Minkin, “Structure and rearrangements of 7-(1,2,3,4,5,6,7-heptaphenylcycloheptatrienyl) isocyanate, isothiocyanate and isoselenocyanate”, Mendeleev Commun., 9:6 (1999), 222–225
Linking options:
https://www.mathnet.ru/eng/mendc4607
https://www.mathnet.ru/eng/mendc/v9/i6/p222
This publication is cited in the following 15 articles:
G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “Reversible Migrations of Nitro Group in a Methyltetramethoxycarbonylcyclopentadiene System”, Dokl Chem, 479:2 (2018), 53
G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “Structure and Rearrangements of 7-(Heptaphenylcycloheptatrienyl)isochalcogencyanates”, Russ J Org Chem, 54:8 (2018), 1134
G.A. Dushenko, I.E. Mikhailov, O.I. Mikhailova, R.M. Minyaev, V.I. Minkin, “STRUKTURA I PEREGRUPPIROVKI 7-(GEPTAFENILTsIKLOGEPTATRIENIL)IZOKhALKOGENTsIANATOV, “Zhurnal organicheskoi khimii””, Zhurnal organicheskoi khimii, 2018, no. 8, 1127
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, “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, “Sigmatropic hydrogen shifts in aryltetraphenylcyclopentadienes”, Dokl Chem, 471:2 (2016), 350
G. A. Dushenko, I. E. Mikhailov, Yu. M. Artyushkina, O. I. Mikhailova, V. V. Tkachev, S. M. Aldoshin, V. I. Minkin, “Quantum-chemical simulation of structure and conformational flexibility of 5,7-di(tert-butyl)-2-(8-hydroxyquinolin-2-yl)-1,3-tropolone”, Russ J Gen Chem, 86:6 (2016), 1306
G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “Structural and stereochemical nonrigidity of 7-(heptaphenylcycloheptatrienyl) isothiocyanate”, Dokl Chem, 466:2 (2016), 35
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
G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “Unidirectional migration of the iodine atom over a cyclopentadiene ring in a rotating electric field”, Mendeleev Commun., 25:1 (2015), 21–23
Akio Toshimitsu, Patai's Chemistry of Functional Groups, 2013
G. A. Dushenko, O. I. Mikhailova, I. E. Mikhailov, R. M. Minyaev, V. I. Minkin, “Rearrangements of cyclopentadienyl cyanates, isocyanates and their thio-,seleno-, and telluro-analogs”, Russ Chem Bull, 58:8 (2009), 1713
O. I. Mikhailova, G. A. Dushenko, I. E. Mikhailov, R. M. Minyaev, V. I. Minkin, “Theoretical and experimental studies on the structure and isomerization of isocyano and cyano cyclopolyenes”, Russ J Org Chem, 44:10 (2008), 1451
I. A. Profatilova, A. A. Bumber, I. E. Mikhailov, G. A. Dushenko, M. P. Bubnov, V. K. Cherkasov, “Electrochemical transformations of cycloheptatriene derivatives”, Russ J Electrochem, 44:7 (2008), 812
Galina A. Dushenko, Igor E. Mikhailov, Adolf Zschunke, Gunter Reck, Burkhard Schulz, Vladimir I. Minkin, “ChemInform Abstract: Structure and Rearrangements of 7‐(1,2,3,4,5,6,7‐Heptaphenylcycloheptatrienyl) Isocyanate, Isothiocyanate, and Isoselenocyanate.”, ChemInform, 31:21 (2000)
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