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Synthesis of Bis(germacyclopropa)benzenes and Structures of Their Annelated Benzene Rings

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Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
Cite this: Organometallics 2006, 25, 1, 230–235
Publication Date (Web):November 8, 2005
https://doi.org/10.1021/om0507629
Copyright © 2006 American Chemical Society
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Abstract

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Extremely hindered bis(germacyclopropa)benzenes (3a,b; the IUPAC name is 4,8-digermatricyclo[5.1.0.03,5]octa-1,3(5),6-triene) were synthesized as stable crystalline compounds by the reaction of the corresponding dilithiogermane Tbt(Dip)GeLi2 (8; Tbt = 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl, Dip = 2,6-diisopropylphenyl) with 1,2,4,5-tetrabromobenzene. The structures of the two stereoisomeric bis(germacyclopropa)benzenes (3a, cis isomer; 3b, trans isomer) were definitively determined by X-ray crystallographic analysis. The central benzene ring of 3a was found to be folded, in contrast to the planar benzene ring of 3b. The X-ray crystallographic analyses of 3a and 3b and the theoretical calculations for some model molecules revealed that the annelated benzene rings have no distinct bond alternation.

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CIF files giving crystallographic data for 3a,b, including all refinement parameters, bond lengths and angles, and positional and thermal parameters, and text and a figure giving details of variable-temperature 13C NMR studies of 3b. This material is available free of charge via the Internet at http://pubs.acs.org.

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  27. Wen-Zuo Li, Jian-Bo Cheng, Qing-Zhong Li, Bao-An Gong, Jia-Zhong Sun. Theoretical investigation on structures and isomerizations of the aluminum chlorogermylenoid H2GeClAlCl2. Journal of Organometallic Chemistry 2009, 694 (18) , 2898-2901. https://doi.org/10.1016/j.jorganchem.2009.04.023
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  30. Wen-Zuo Li, Bao-An Gong, Jian-Bo Cheng, Cui-Ping Xiao. Theoretical study on the beryllium chlorogermylenoid H2GeClBeCl. Journal of Molecular Structure: THEOCHEM 2007, 847 (1-3) , 75-78. https://doi.org/10.1016/j.theochem.2007.08.036
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