Hückel and Möbius aromaticity and trimerous transition state behaviour in the pericyclic reactions of [10], [14], [16] and [18]annulenes

Sonsoles Martín-Santamaría; Balasundaram Lavan; Henry S. Rzepa

doi:10.1039/B002082F

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Journal of the Chemical Society, Perkin Transactions 2

Issue 7, 2000

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Hückel and Möbius aromaticity and trimerous transition state behaviour in the pericyclic reactions of [10], [14], [16] and [18]annulenes

Sonsoles Martín-Santamaría , Balasundaram Lavan and Henry S. Rzepa

J. Chem. Soc., Perkin Trans. 2, 2000, 1415-1417

DOI: 10.1039/B002082F
Received 14 Mar 2000, Accepted 13 Apr 2000
First published on the web 01 Jun 2000

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Abstract
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The pericyclic reactions of a series of [n]annulenes (n = 10, 14, 16, 18) reveal unusual differences in their behaviour related to their aromaticity. For n = 10, 14, synchronous pericyclic bond formation (trimerous behaviour) is possible, whereas the synchronicity is not apparent for n = 18. The formally anti-aromatic system n = 16 exhibits valence bond isomerism, asynchronous pericyclisation and a novel conformation which appears to be an example of a Heilbronner Möbius aromatic, as indicated by nucleus independent chemical shift calculations.

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Journal of the Chemical Society, Perkin Transactions 2

Hückel and Möbius aromaticity and trimerous transition state behaviour in the pericyclic reactions of [10], [14], [16] and [18]annulenes

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Journal of the Chemical Society, Perkin Transactions 2

Hückel and Möbius aromaticity and trimerous transition state behaviour in the pericyclic reactions of [10], [14], [16] and [18]annulenes

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