Abstract:
Fast and reversible migrations of the ethoxydithiocarbonate group along the perimeter of the cycloheptatriene ring of 3 have been found to occur through a series of successive 1,7-sigmatropic shifts with an energy barrier in the range 17.4–17.9 kcal mol–1.
Document Type:
Article
Language: English
Citation:
G. A. Dushenko, I. E. Mikhailov, A. Zschunke, N. Hakam, C. Muegge, V. I. Minkin, “Fluxional Behaviour of 7-Cyclohepta-1,3,5-trienyl Ethoxydithiocarbonate”, Mendeleev Commun., 5:4 (1995), 133–134
Linking options:
https://www.mathnet.ru/eng/mendc5065
https://www.mathnet.ru/eng/mendc/v5/i4/p133
This publication is cited in the following 11 articles:
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 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, “Sigmatropic hydrogen shifts in aryltetraphenylcyclopentadienes”, Dokl Chem, 471:2 (2016), 350
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
Sergei M. Lukyanov, Alla V. Koblik, Patai's Chemistry of Functional Groups, 2009
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
E. Kleinpeter, Comprehensive Organic Functional Group Transformations II, 2005, 495
V. I. Minkin, I. E. Mikhailov, G. A. Dushenko, O. E. Kompan, A. Zschunke, “Fast and reversible migrations of N,S-centered groups around the perimeter of cyclopropene and cycloheptatriene rings”, Russ Chem Bull, 47:5 (1998), 884
Ilya D. Gridnev, Oleg L. Tok, Natalya A. Gridneva, Yuri N. Bubnov, Peter R. Schreiner, “Synthesis and Dynamic Properties of Cycloheptatrienyl(dipropyl)borane. Equilibrium with 7-Dipropylborylnorcaradiene”, J. Am. Chem. Soc., 120:5 (1998), 1034
G. A. Dushenko, I. E. Mikhailov, A. Zschunke, N. Hakam, C. Muegge, V. I. Minkin, “1,7-Sigmatropic shifts of the phenylsulfanyl group along the perimeter of the cycloheptatriene ring”, Mendeleev Commun., 7:2 (1997), 50–51
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