4.8 Article

Are antiaromatic rings stacked face-to-face aromatic?

Journal

ORGANIC LETTERS
Volume 9, Issue 17, Pages 3263-3266

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol071183y

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The stacking of 4n pi electron hydrocarbon rings into superphane structures can eliminate their antiaromaticity and result in through-space three-dimensional aromatic character. This is demonstrated by the bond length equalized geometries and diatropic NICS values of the methano-bridged superphane series with interacting three- to nine-membered 4n pi electron rings. Along with triplet and Mobius strategies, stacking is the third way to achieve aromatic ring systems with 4n pi electrons.

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