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Issue 33, 2008
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Synthesis and properties of stable 2-metallanaphthalenes of heavier group 14 elements†‡§

Yoshiyuki Mizuhata,a   Takahiro Sasamori,a   Noriyoshi Nagahora,ab   Yasuaki Watanabe,c   Yukio Furukawac  and  Norihiro Tokitoh*a  
Author affiliations

* Corresponding authors

a Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, Japan
E-mail: tokitoh@boc.kuicr.kyoto-u.ac.jp
Fax: +81-774-38-3209
Tel: +81-774-38-3200

b Institute of Sustainability Science, Kyoto University, Gokasho, Uji, Kyoto, Japan
E-mail: nagahora@iss.iae.kyoto-u.ac.jp
Fax: +81-774-38-3209
Tel: +81-774-38-3218

c Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo, Japan
E-mail: furukawa@waseda.jp
Fax: +81-3-3208-7022
Tel: +81-3-5286-3244

Abstract

The first stable neutral stannaaromatic compound, 2-stannanaphthalene 1a, was synthesized by taking advantage of an extremely bulky and efficient steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt). The molecular structure and aromaticity of 1a were discussed on the basis of X-ray crystallographic analysis, NMR, UV-vis, and Raman spectroscopy, cyclic voltammetry, and theoretical calculations. 2-Germanaphthalene 2a, which has a framework similar to that of 1a, was synthesized for comparison, and systematic elucidation was made for the properties of 2-metallanaphthalene systems containing a heavier group 14 element (Si, Ge, or Sn).

Graphical abstract: Synthesis and properties of stable 2-metallanaphthalenes of heavier group 14 elements

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Article information

https://doi.org/10.1039/B718193K
Submitted
26 Nov 2007
Accepted
25 Jan 2008
First published
02 Jul 2008
Dalton Trans., 2008, 4409-4418
Article type
Paper
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Synthesis and properties of stable 2-metallanaphthalenes of heavier group 14 elements

Y. Mizuhata, T. Sasamori, N. Nagahora, Y. Watanabe, Y. Furukawa and N. Tokitoh, Dalton Trans., 2008, 4409
DOI: 10.1039/B718193K

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