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Degenerate Rearrangement of Long-Lived 9,10-Dimethyl-9-(cis-1-methyl-1-propenyl)phenanthrenium Ion: 1,2-Shift of the Dimethylvinyl Group

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Abstract

Dynamic NMR study showed that 9,10-dimethyl-9-(cis-1-methyl-1-propenyl)phenanthrenium ion generated by reaction of 1,2,2a,10b-tetramethyl-2a,10b-dihydrocyclobuta[l]phenanthrene with HSO3F below -100°C undergoes very fast (ΔG≠ = 22 kJ/mol at -120°C ) degenerate 1,2-shift of the dimethylvinyl group.

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Authors
  1. V. A. Bushmelev
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  2. A. M. Genaev
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  3. V. G. Shubin
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Bushmelev, V.A., Genaev, A.M. & Shubin, V.G. Degenerate Rearrangement of Long-Lived 9,10-Dimethyl-9-(cis-1-methyl-1-propenyl)phenanthrenium Ion: 1,2-Shift of the Dimethylvinyl Group. Russian Journal of Organic Chemistry 40, 966–972 (2004). https://doi.org/10.1023/B:RUJO.0000045186.11978.a5

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