Issue 17, 2004
From the journal:

Organic & Biomolecular Chemistry

Kinetic stabilization of the o-quinoidal 3,4-benzotropone system

Masakazu Ohkita,*a   Kieko Sano,b   Katsuhiko Ono,a   Katsuhiro Saito,a   Takanori Suzukib  and  Takashi Tsujib  

* Corresponding authors

a Graduate School of Engineering, Nagoya Institute of Technology, Nagoya, Japan
E-mail: ohkita.masakazu@nitech.ac.jp
Fax: +81-(0)52-735-5604
Tel: +81-(0)52-735-5604

b Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, Japan

Abstract

Kinetic stabilization of the o-quinoidal 3,4-benzotropone system was investigated. The parent 3,4-benzotropone 1 undergoes rapid [π8 + π10] dimerization in fluid solution even at −78 °C while triptycene-fused derivative 5 having a tert-butyl group at the C(6) position of the tropone moiety was found to be stable indefinitely under similar conditions. The relative importance of the triptycene moiety and the tert-butyl group in 5 for the kinetic stabilization was evaluated.

Graphical abstract: Kinetic stabilization of the o-quinoidal 3,4-benzotropone system

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Article information

DOI
https://doi.org/10.1039/B408393H
Article type
Paper
Submitted
02 Jun 2004
Accepted
24 Jun 2004
First published
02 Aug 2004

Org. Biomol. Chem., 2004,2, 2421-2425

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Kinetic stabilization of the o-quinoidal 3,4-benzotropone system

M. Ohkita, K. Sano, K. Ono, K. Saito, T. Suzuki and T. Tsuji, Org. Biomol. Chem., 2004, 2, 2421 DOI: 10.1039/B408393H

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