Synthesis and Characterization of Two Isomers of 14π-Electron Germaaromatics: Kinetically Stabilized 9-Germaanthracene and 9-Germaphenanthrene
- Takahiro Sasamori ,
- Koji Inamura ,
- Wataru Hoshino ,
- Norio Nakata ,
- Yoshiyuki Mizuhata ,
- Yasuaki Watanabe ,
- Yukio Furukawa , and
- Norihiro Tokitoh
View Author Information
Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan, and Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan
Abstract
The first stable 9-germaanthracene and 9-germaphenanthrene were successfully synthesized by taking advantage of kinetic stabilization utilizing effective steric protection groups, Tbt and Bbt groups (Tbt = 2,4,6-tris[bis(trimeth-ylsilyl)methyl]phenyl, Bbt = 2,6-bis[bis(trimethylsilyl)methyl]-4-[tris(trimethylsilyl)methyl]phenyl). The similarities and differences of the structures and properties between the two isomers of germaaromatics are discussed.
†
Kyoto University.
‡
Waseda University.
*
To whom correspondence should be addressed. Phone: +81-774-38-3200. Fax: +81-774-38-3209. E-mail: [email protected]
Cited By
This article is cited by 28 publications.
- Ming-Der Su . Mechanistic Study of the Photochemical Isomerization Reactions of Silabenzene. Organometallics 2014, 33 (19) , 5231-5237. https://doi.org/10.1021/om500545a
- Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh. Generation of Stannabenzenes and Their Properties. Organometallics 2010, 29 (21) , 4781-4784. https://doi.org/10.1021/om100382n
- Takeshi Matsumoto, Takahiro Sasamori, Kazunobu Sato, Takeji Takui and Norihiro Tokitoh. Reduction of a Kinetically Stabilized Silabenzene Leading to the Formation of the Corresponding Anion Radical Species. Organometallics 2008, 27 (3) , 305-308. https://doi.org/10.1021/om701060a
- Norihiro Tokitoh,, Akihiro Shinohara,, Takeshi Matsumoto,, Takahiro Sasamori,, Nobuhiro Takeda, and, Yukio Furukawa. Synthesis and Properties of a Kinetically Stabilized 9-Silaphenanthrene. Organometallics 2007, 26 (16) , 4048-4053. https://doi.org/10.1021/om700347z
- J. Robin Fulton. Germanium, Tin and Lead. 2020,,https://doi.org/10.1016/B978-0-12-409547-2.14900-5
- . Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. 2020,,https://doi.org/
- Yoshiyuki Mizuhata, Norihiro Tokitoh. Silaaromatics and Related Compounds. 2017,,, 619-641. https://doi.org/10.1016/B978-0-12-801981-8.00010-1
- . Organosilicon Compounds. 2017,,https://doi.org/
- Yoshiyuki Mizuhata, Koji Inamura, Norihiro Tokitoh. Coordination chemistry of 9-sila- and 9-germa-phenanthrenes — unique coordination modes in their metallene complexes. Canadian Journal of Chemistry 2014, 92 (6) , 441-446. https://doi.org/10.1139/cjc-2013-0501
- Mark Banaszak Holl, David R. Peck. Germanium: Organometallic Chemistry. 2011,,https://doi.org/10.1002/9781119951438.eibc0075
- . Encyclopedia of Inorganic and Bioinorganic Chemistry. 2011,,https://doi.org/
- Yoshiyuki Mizuhata, Norihiro Tokitoh. Chemistry of Aromatic Compounds Containing a Heavier Group 14 Element. Journal of Synthetic Organic Chemistry, Japan 2011, 69 (6) , 691-704. https://doi.org/10.5059/yukigoseikyokaishi.69.691
- . Heavy Analogs of Aromatic Compounds. 2010,,, 335-414. https://doi.org/10.1002/9780470669266.ch6
- Vladimir Ya. Lee, Akira Sekiguchi. Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb. 2010,,https://doi.org/
- Yoshiyuki Mizuhata, Akihiro Shinohara, Yusuke Tanabe, Norihiro Tokitoh. Cycloaddition Reactions of Kinetically Stabilized 9-Silaanthrancene with Polycyclic Aromatic Hydrocarbons. Chemistry - A European Journal 2009, 15 (34) , 8405-8408. https://doi.org/10.1002/chem.200901290
- Yoshiyuki Mizuhata, Norihiro Tokitoh. Reactions of a kinetically stabilized 2-stannanaphthalene with elemental sulfur and selenium: synthesis of novel cyclic chalcogenides containing a tin atom. Journal of Sulfur Chemistry 2009, 30 (3-4) , 385-392. https://doi.org/10.1080/17415990903033368
- Mark M. Banaszak Holl, David R. Peck. Germanimum: Organometallic Chemistry. 2009,,https://doi.org/10.1002/0470862106.ia080.pub2
- , , , , . Encyclopedia of Inorganic Chemistry. 2006,,https://doi.org/
- Yusuke Tanabe, Yoshiyuki Mizuhata, Norihiro Tokitoh. Mechanistic Investigation of the Hydration Reaction of [Cr(η 6 -silabenzene)(CO) 3 ]: Hydrido(silacyclohexadienyl)chromium Complex as an Intermediate. Chemistry Letters 2008, 37 (7) , 720-721. https://doi.org/10.1246/cl.2008.720
- Norihiro Tokitoh, Keiji Wakita, Takeshi Matsumoto, Takahiro Sasamori, Renji Okazaki, Nozomi Takagi, Masahiro Kimura, Shigeru Nagase. The Chemistry of Stable Silabenzenes. Journal of the Chinese Chemical Society 2008, 55 (3) , 487-507. https://doi.org/10.1002/jccs.200800073
- P. Norris. Six-membered Rings with One Other Element. 2008,,, 1049-1066. https://doi.org/10.1016/B978-008044992-0.00614-3
- . Comprehensive Heterocyclic Chemistry III. 2008,,https://doi.org/
- Yoshiyuki Mizuhata, Takahiro Sasamori, Noriyoshi Nagahora, Yasuaki Watanabe, Yukio Furukawa, Norihiro Tokitoh. Synthesis and properties of stable 2-metallanaphthalenes of heavier group 14 elements. Dalton Transactions 2008, 33 (33) , 4409. https://doi.org/10.1039/b718193k
- Vladimir Ya. Lee, Akira Sekiguchi. Cyclic polyenes of heavy group 14 elements: new generation ligands for transition-metal complexes. Chemical Society Reviews 2008, 37 (8) , 1652. https://doi.org/10.1039/b800580j
- Vladimir Ya. Lee, Akira Sekiguchi. Aromatizität von metallorganischen Verbindungen mit Gruppe-14-Elementen: experimentelle Aspekte. Angewandte Chemie 2007, 119 (35) , 6716-6740. https://doi.org/10.1002/ange.200604869
- Vladimir Ya. Lee, Akira Sekiguchi. Aromaticity of Group 14 Organometallics: Experimental Aspects. Angewandte Chemie International Edition 2007, 46 (35) , 6596-6620. https://doi.org/10.1002/anie.200604869
- Norihiro Tokitoh, Norio Nakata, Akihiro Shinohara, Nobuhiro Takeda, Takahiro Sasamori. Coordination Chemistry of a Kinetically Stabilized Germabenzene: Syntheses and Properties of Stable η6-Germabenzene Complexes Coordinated to Transition Metals. Chemistry - A European Journal 2007, 13 (6) , 1856-1862. https://doi.org/10.1002/chem.200601196
- J. Parr. Carbon, silicon, germanium, tin and lead. Annual Reports Section "A" (Inorganic Chemistry) 2007, 103 , 90. https://doi.org/10.1039/b612602m