Abstract:
Rapid and reversible migrations of the phenylsulfanyl group around the seven-membered ring of 7-phenylsulfanylcyclohepta- 1,3,5-triene have been proved to proceed through successive 1,7-sigmatropic shifts with an energy barrier (ΔG≠298) in the range of 19.5−20.1 kcal mol–1.
Document Type:
Article
Language: English
Citation:
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
Linking options:
https://www.mathnet.ru/eng/mendc4777
https://www.mathnet.ru/eng/mendc/v7/i2/p50
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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, “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, “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, “Mechanisms of rearrangements of substituted thiocyclopropenes”, Dokl Chem, 452:1 (2013), 220
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
Stuart T. Caldwell, Hanna M. Petersson, Louis J. Farrugia, William Mullen, Alan Crozier, Richard C. Hartley, “Isotopic labelling of quercetin 3-glucoside”, Tetrahedron, 62:31 (2006), 7257
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
Ian D. Cunningham, “Chapter 9. Reaction mechanisms . Part (ii) Pericyclic reactions”, Annu. Rep. Prog. Chem., Sect. B, 94 (1998), 273
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
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