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Synlett 2016; 27(14): 2128-2132
DOI: 10.1055/s-0035-1561473
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© Georg Thieme Verlag Stuttgart · New York

Bowl-to-Bowl Inversion Accelerated by the Introduction of Bulky 1,1,4,4-Tetramethylbutane-1,4-diyl Groups on Sumanene

Toru Amaya*
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka 565-0871, Japan   eMail: amaya@chem.eng.osaka-u.ac.jp   eMail: hirao@chem.eng.osaka-u.ac.jp
,
Shun Katoh
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka 565-0871, Japan   eMail: amaya@chem.eng.osaka-u.ac.jp   eMail: hirao@chem.eng.osaka-u.ac.jp
,
Toshikazu Hirao*
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka 565-0871, Japan   eMail: amaya@chem.eng.osaka-u.ac.jp   eMail: hirao@chem.eng.osaka-u.ac.jp
b   The Institute of Scientific and Industrial Research, Osaka University, Mihoga-oka, Ibaraki, Osaka 567-0047, Japan
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Publikationsverlauf

Received: 08. April 2016

Accepted after revision: 15. Mai 2016

Publikationsdatum:
22. Juni 2016 (online)

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Abstract

A variable-temperature 1H NMR study revealed that the bowl-to-bowl inversion of sumanene is accelerated by the introduction of bulky 1,1,4,4-tetramethylbutane-1,4-diyl groups on the peripheral aromatic ring. This is likely to be induced by a bowl flattening, as shown in the DFT-optimized structures.

Key words

bowl-to-bowl inversion - sumanene - bowl-shaped polyaromatic molecule - Friedel–Crafts alkylation - variable-temperature 1H NMR

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561473.
  • Supporting Information

Primary Data

    Primary data for this article are available online at http://www.thieme-connect.com/products/ejournals/journal/10.1055/s-00000083 and can be cited using the following DOI: 10.4125/pd0079th.
  • Primary Data
 

  • References and Notes

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