- Substituent Effect Behavior in the Antiaromatic Inden-1-yl Cation System
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Studies of the rate-accelerating effects in solvolysis produced by 5-methyl and 5-methoxy substituents on the benzene ring and a 3-methyl substituent on the double bond of the inden-1-yl 3,5-dinitrobenzolate system have been carried out.In both 80percent aqueous acetone and in 2,2,2-trifluoroethanol, the rate accelerations observed in the inden-1-yl system were approximately the same as those found in model cyclopenten-3-yl and indan-1-yl systems.From these results, it is concluded that delocalization of charge into both the benzene ring and double bond of the 8?-electron inden-1-yl carbocation is taking place and is apparently undiminished by antiaromatic effects.
- Friedrich, Edwin C.,Tam, Teresa M.
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p. 315 - 319
(2007/10/02)
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