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Issue 3, 2018
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1,2-Dihalodigermenes bearing bulky Eind groups: synthesis, characterization, and conversion to halogermylenoids†

Naoki Hayakawa,a   Tomohiro Sugahara,b   Yasuyuki Numata,a   Hotaka Kawaai,a   Kenta Yamatani,a   Shogo Nishimura,a   Shun Goda,a   Yuko Suzuki,b   Tomoharu Tanikawa,a   Hidetaka Nakai, ORCID logo a   Daisuke Hashizume, ORCID logo c   Takahiro Sasamori, ORCID logo *bd   Norihiro Tokitoh ORCID logo b  and  Tsukasa Matsuo ORCID logo *a  
Author affiliations

* Corresponding authors

a Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
E-mail: t-matsuo@apch.kindai.ac.jp

b Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan

c Materials Characterization Support Unit, RIKEN Center for Emergent Matter Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

d Graduate School of Natural Sciences, Nagoya City University, Yamanohata 1, Mizuho-cho, Mizuho-ku, Nagoya, Aichi 467-8501, Japan
E-mail: sasamori@nsc.nagoya-cu.ac.jp

Abstract

1,2-Dihalodigermenes, (E)-(Eind)XGe[double bond, length as m-dash]GeX(Eind) (X = Br and Cl), bearing the fused-ring bulky Eind group (Eind = 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl) have been isolated as orange-yellow crystals by the ligand redistribution reaction between the diarylgermylene, (Eind)2Ge:, and GeX2·dioxane in toluene via the cleavage and recombination of the Ge–C and Ge–X bonds. The dihalodigermenes have a Ge[double bond, length as m-dash]Ge double bond character in the crystalline state, but dissociate into halogermylenes, (Eind)XGe:, in solution. The addition of excess LiBr to the THF solution of the bromogermylene, (Eind)BrGe:, led to the formation of an equilibrium mixture containing the lithium bromogermylenoid, [Li+][(Eind)GeBr2]−. The bromogermylenoid can be isolated as a cryptand-separated potassium ion pair, [K+(crypt-222)][(Eind)GeBr2]−, which has been structurally characterized.

Graphical abstract: 1,2-Dihalodigermenes bearing bulky Eind groups: synthesis, characterization, and conversion to halogermylenoids

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Article information

https://doi.org/10.1039/C7DT03819D
Submitted
11 Oct 2017
Accepted
07 Dec 2017
First published
08 Dec 2017
Dalton Trans., 2018,47, 814-822
Article type
Paper
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1,2-Dihalodigermenes bearing bulky Eind groups: synthesis, characterization, and conversion to halogermylenoids

N. Hayakawa, T. Sugahara, Y. Numata, H. Kawaai, K. Yamatani, S. Nishimura, S. Goda, Y. Suzuki, T. Tanikawa, H. Nakai, D. Hashizume, T. Sasamori, N. Tokitoh and T. Matsuo, Dalton Trans., 2018, 47, 814
DOI: 10.1039/C7DT03819D

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