The Journal of organic chemistry

Dications of fluorenylidenes. relationship between electrochemical oxidation potentials and antiaromaticity in diphenyl-substituted fluorenyl cations

NS Mills, MA Benish, C Ybarra

Index: Mills, Nancy S.; Benish, Michele A.; Ybarra, Christie Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2003 - 2012

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Citation Number: 32

Abstract

The antiaromaticity of a series of dications of p-substituted diphenylmethylidene fluorenes was explored using three criteria attributed to aromaticity/antiaromaticity. The relative stability of the dications (energetic criterion) was measured via the redox potentials obtained by electrochemical oxidation under very fast sweep rates with microelectrodes. Comparison of redox potentials with those of a model system, p-substituted tetraphenylethylenes, ...