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Sila- and Germacyclopropabenzenes

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Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
Cite this: Organometallics 2006, 25, 15, 3522–3532
Publication Date (Web):June 17, 2006
https://doi.org/10.1021/om060158d
Copyright © 2006 American Chemical Society
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Abstract

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This review article describes the initial work on the sila- and germacyclopropabenzenes, the heavier congeners of cyclopropabenzenes that have a silicon or germanium atom instead of a carbon atom as the bridging atom of its cyclopropabenzene skeleton. The key factor in their successful preparation is the development of a synthetic method that is effective under mild conditions, i.e., the reaction of a dilithio compound (Tbt(Dip)MLi2 (M = Si, Ge)) that has effective steric protective groups, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (denoted as Tbt) and 2,6-diisopropylphenyl (denoted as Dip), with 1,2-dibromobenzene at −78 °C. These were successfully applied to the synthesis of not only sila- and germacyclopropabenzenes but also stable bis(sila- and germacyclopropa)benzenes with two sila- and germacyclopropene rings fused to one benzene ring. These compounds are the heavier congeners of the unknown bis(cyclopropa)benzene derivative.

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Cited By

This article is cited by 32 publications.

  1. Alexander C. Filippou, Kai W. Stumpf, Oleg Chernov, and Gregor Schnakenburg . Metal Activation of a Germylenoid, a New Approach to Metal–Germanium Triple Bonds: Synthesis and Reactions of the Germylidyne Complexes [Cp(CO)2M≡Ge–C(SiMe3)3] (M = Mo, W). Organometallics 2012, 31 (2) , 748-755. https://doi.org/10.1021/om201176n
  2. Taro Tanabe, Yoshiyuki Mizuhata, Nobuhiro Takeda and Norihiro Tokitoh. Syntheses and Structures of Platinum Siloxides Bridged by a Sulfur or Selenium Atom and a Unique 1,3-Aryl Migration from Silicon to Platinum through the Si−O−Pt Linkages. Organometallics 2008, 27 (10) , 2156-2158. https://doi.org/10.1021/om800210g
  3. Xiao-Lin Zhang, Ming-Xia Zhang, Bing-Fei Yan, Wen-Zuo Li. A Spiro-Ge-Heterocyclic Compound Formation via Germylenoid and Formaldehyde: A Theoretical Study. Russian Journal of Physical Chemistry A 2020, 94 (10) , 2084-2090. https://doi.org/10.1134/S0036024420100349
  4. Mingxia Zhang, Wenzuo Li, Qingzhong Li, Jianbo Cheng. The addition reactions of germylenoid H2GeAlCl3 with ethylene: a theoretical investigation. Journal of Molecular Modeling 2017, 23 (7) https://doi.org/10.1007/s00894-017-3375-z
  5. Ming-Xia Zhang, Bing-Fei Yan, Wen-Zuo Li, Qing-Zhong Li, Jian-Bo Cheng. Structures of the germylenoid H2GeZnCl2 and its addition reactions with ethylene. Structural Chemistry 2016, 27 (6) , 1819-1829. https://doi.org/10.1007/s11224-016-0802-1
  6. Yuko Suzuki, Takahiro Sasamori, Jing-Dong Guo, Shigeru Nagase, Norihiro Tokitoh. Isolation and Ambident Reactivity of a Chlorogermylenoid. Chemistry - A European Journal 2016, 22 (39) , 13784-13788. https://doi.org/10.1002/chem.201602601
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  9. Gongxiao Zhang, Yuhua Qi, Chongjuan Xu. Theoretical study on the substitution reactions of the germylenoid H2GeLiF with SiH3X (X = F, Cl, Br). Journal of Molecular Modeling 2016, 22 (6) https://doi.org/10.1007/s00894-016-2997-x
  10. Ming-Xia Zhang, Bing-Fei Yan, Wen-Zuo Li, Qing-Zhong Li, Jian-Bo Cheng. Theoretical prediction on the addition reaction of germylenoid H 2 GeFMgF with ethylene. Journal of Theoretical and Computational Chemistry 2016, 15 (03) , 1650022. https://doi.org/10.1142/S021963361650022X
  11. Ming-Xia Zhang, Cui-Ping Xiao, Zhen-Bo Liu, Wen-Zuo Li, Qing-Zhong Li, Jian-Bo Cheng. Theoretical prediction on the insertion reactions of the germylenoid H2GeLiF with GeH3X (X = F, Cl, Br). Russian Journal of Physical Chemistry A 2015, 89 (10) , 1872-1877. https://doi.org/10.1134/S0036024415100234
  12. Tong-Tong Wang, Wen-Zuo Li, Qing-Zhong Li, Jian-Bo Cheng. Theoretical prediction on H2 elimination reactions of H2GeLiF with RH (R = Cl, SH, and PH2). Russian Journal of Physical Chemistry A 2015, 89 (5) , 812-817. https://doi.org/10.1134/S0036024415050325
  13. Bingfei Yan, Wenzuo Li, Cuiping Xiao, Zhenbo Liu, Qingzhong Li, Jianbo Cheng. New insights into the insertion reactions of germylenoid H2GeLiF with RH (R = F, OH, NH2). Journal of Molecular Modeling 2015, 21 (4) https://doi.org/10.1007/s00894-015-2626-0
  14. Ming-Xia Zhang, Ming-Jun Zhang, Wen-Zuo Li, Qing-Zhong Li, Jian-Bo Cheng. Structure of H 2 GeFMgF and its insertion reactions with RH ( R = F , OH , NH 2 ). Journal of Theoretical and Computational Chemistry 2015, 14 (01) , 1550004. https://doi.org/10.1142/S0219633615500042
  15. Cui-Ping Xiao, Wen-Zuo Li, Qing-Zhong Li, Jian-Bo Cheng. Substitution reactions of H2GeFBeF with RH (R = F, OH, NH2): A theoretical study. Russian Journal of Physical Chemistry A 2014, 88 (7) , 1097-1102. https://doi.org/10.1134/S0036024414070103
  16. Cem Burak Yıldız, Akın Azizoglu. Computational investigations on the electronic and structural properties of germacyclopropylidenoids. Computational and Theoretical Chemistry 2013, 1023 , 24-28. https://doi.org/10.1016/j.comptc.2013.09.009
  17. Bingfei Yan, Wenzuo Li, Cuiping Xiao, Qingzhong Li, Jianbo Cheng. A new reaction mode of germanium-silicon bond formation: insertion reactions of H2GeLiF with SiH3X (X = F, Cl, Br). Journal of Molecular Modeling 2013, 19 (10) , 4537-4543. https://doi.org/10.1007/s00894-013-1970-1
  18. BING-FEI YAN, WEN-ZUO LI, YU-WEI PEI, QING-ZHONG LI, JIAN-BO CHENG. THEORETICAL INVESTIGATION ON THE INSERTION REACTIONS OF THE GERMYLENOID H 2 GeLiF WITH RH ( R = Cl , SH , PH 2 ). Journal of Theoretical and Computational Chemistry 2013, 12 (03) , 1350003. https://doi.org/10.1142/S021963361350003X
  19. Wen-Zuo Li, Bing-Fei Yan, Qing-Zhong Li, Jian-Bo Cheng. The insertion reactions of the germylenoid H2GeLiF with CH3X (X = F, Cl, Br). Journal of Organometallic Chemistry 2013, 724 , 163-166. https://doi.org/10.1016/j.jorganchem.2012.11.012
  20. Wen-Zuo Li, Yu-Wei Pei, Jian-Bo Cheng, Qing-Zhong Li, Bao-An Gong. Theoretical study on the insertion reactions of the germylenoid H2GeClMgCl with RH (R = F, OH, NH2). Russian Journal of Physical Chemistry A 2012, 86 (13) , 1969-1973. https://doi.org/10.1134/S0036024412130225
  21. Wen-Zuo Li, Quan-Zhen Cao, Yu-Wei Pei, Ran Li, Hong-Jie Zhu, Qing-Zhong Li, Jian-Bo Cheng. Theoretical study on germylenoid H2GeFBeF. Structural Chemistry 2012, 23 (3) , 867-871. https://doi.org/10.1007/s11224-011-9933-6
  22. Yuhua Qi, Bing Geng, Zhonghe Chen. The structures and stability of pentacoordinate germylenoid PhCH2(NH2)CH3GeLiF. Structural Chemistry 2011, 22 (4) , 917-924. https://doi.org/10.1007/s11224-011-9779-y
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  24. Wen-Zuo Li, Tao Liu, Jian-Bo Cheng, Qing-Zhong Li, Bao-An Gong. Theoretical investigation on H2 elimination reactions of germylenoid H2GeLiF with RH (R=F, OH, and NH2). Journal of Organometallic Chemistry 2010, 695 (6) , 909-912. https://doi.org/10.1016/j.jorganchem.2010.01.016
  25. 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
  26. Taro Tanabe, Yoshiyuki Mizuhata, Nobuhiro Takeda, Norihiro Tokitoh. Syntheses and structures of overcrowded silanedichalcogenols and their applications to the syntheses of silanedichalcogenolato complexes. Journal of Organometallic Chemistry 2009, 694 (3) , 353-365. https://doi.org/10.1016/j.jorganchem.2008.11.001
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