Substituent Effect Behavior in the Antiaromatic Inden-1-yl Cation System

Article abstract of DOI:10.1021/jo00341a027

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.