Degenerate rearrangement of 9-isopropenyl-9, 10-dimethyl-phenanthren-9-yl and 9, 10-dimethyl-9-(trans-1-methylprop-1-en-1-yl) phenanthren-9-yl cations

VG Artamoshkin, VA Bushmelev, AM Genaev…

文献索引：Artamoshkin; Bushmelev; Genaev; Shubin Russian Journal of Organic Chemistry, 2006 , vol. 42, # 9 p. 1257 - 1263

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被引用次数: 9

摘要

Abstract 1 H NMR study has shown that long-lived 9-R-9, 10-dimethylphenanthren-9-yl cations (R= isopropenyl, trans-1-methylprop-1-en-1-yl) generated in the system HSO 3 F-SO 2 ClF-CD 2 Cl 2 at− 130° C undergo degenerate rearrangement via 1, 2-vinyl shifts (Δ G'= 37 and 39 kJ/mol, respectively, at− 88° C). Analysis of the geometric parameters of the initial structures and transition states calculated by the DFT method indicates that unfavorable ...