Synthesis and Isolation of the First Germacyclopropabenzene: A Study to Elucidate the Intrinsic Factor for the Ring Deformation of Cyclopropabenzene Skeletons
- Norihiro Tokitoh ,
- Ken Hatano ,
- Takayo Sasaki ,
- Takahiro Sasamori ,
- Nobuhiro Takeda ,
- Nozomi Takagi , and
- Shigeru Nagase
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Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan, Institute for Fundamental Research of Organic Chemistry, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan, and Institute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan
Abstract
The treatment of an overcrowded diaryldilithiogermane, Tbt(Dip)GeLi2 (Tbt = 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl; Dip = 2,6-diisopropylphenyl), generated by exhaustive reduction of the corresponding dibromogermane Tbt(Dip)GeBr2, with 1,2-dibromobenzene resulted in the isolation of the first stable germacyclopropabenzene, which was fully characterized by 1H and 13C NMR spectra, FAB-MS, and X-ray structural analysis. As for the ring deformation of cyclopropabenzene and its heavier group 14 element analogues, the experimental results are in good agreement with those obtained by theoretical calculations.
*
To whom correspondence should be addressed. E-mail: [email protected] boc.kuicr.kyoto-u.ac.jp. Tel: +81-774-38-3200. Fax: +81-774-38-3209.
†
Kyoto University.
‡
Kyushu University.
§
Institute for Molecular Science.
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