Synthesis of Zethrene Derivatives by Transannular Cyclization of Tetradehydrodinaphtho[10]annulene and their Physical Properties

• Project/Area Number: 21750046
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kansai University
• Principal Investigator: UMEDA Rui Kansai University, 化学生命工学部, 助教 (70467512)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000); Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2009: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
• Keywords: 多環式芳香族化合物 / アセチレン / 渡環環化反応 / ゼトレン / デヒドロアヌレン

Research Abstract

The synthesis and structural characterization of hitherto unknown tetradehydrodinaphtho[10]annulene was achieved for the first time. Moreover, the dinaphtho[10]annulene was transformed smoothly into stable zethrene derivatives substituted at its 7,14-positions, showing that it serves as a good reservoir of zethrene derivatives. Optical and electrochemicalproperties of a disubstituted zethrene derivative are also investigated.

Research Products

• [Journal Article] Fritsch-Buttenberg-Wiechell rearrangement to alkynes from gem-dihalo alkenes with lanthanum metal (2011)
  • Author(s): 梅田塁
  • Journal Title: Journal of Organometallic Chemistry Volume: (印刷中)
  • Peer Reviewed
• [Journal Article] Selenium-Catalyzed Reductive Cyclization and Carbocyclization of 2,2'-Dinitrostilbenes with Carbon Monoxide : One-Shot Synthesis of Indolo[1,2-c]quinazolinones (2011)
  • Author(s): 梅田塁
  • Journal Title: Heteroatom Chemistry Volume: (印刷中)
  • Peer Reviewed
• [Journal Article] PtCl_2-Catalyzed Cyclization of o-Diethynylbenzene Derivatives Triggered by Intramolecular Nucleophilic Attack (2011)
  • Author(s): 三木康嗣
  • Journal Title: Synthetic Communication Volume: 41 Pages: 1077-1087
  • Peer Reviewed
• [Journal Article] Rhenium Complex as a Useful Catalyst for Acylative Cleavage of Ethers (2011)
  • Author(s): 梅田塁
  • Journal Title: Synlett Pages: 3089-3091
  • Peer Reviewed
• [Journal Article] 古くて新しい芳香族化合物～有機エレクトロニクス材料への応用～ (2010)
  • Author(s): 梅田塁
  • Journal Title: 理工学と技術(関西大学理工学会誌) vol.17 Pages: 33-36
  • NAID: 110009591576
• [Journal Article] Tetradehydrodinaphtho-[10]annulene and its Transformation into Zethrene : A Hitherto Unknown Dehydroannulene and a Forgotten Aromatic Hydrocarbon (2010)
  • Author(s): Rui Umeda, Daijiro Hibi, Koji Miki, Yoshito Tobe
  • Journal Title: Pure Appl.Chem. 82 Pages: 871-878
  • Peer Reviewed
• [Journal Article] 古くて新しい芳香族化合物～有機エレクトロニクス材料への応用～ (2010)
  • Author(s): 梅田塁
  • Journal Title: 理工学と技術(関西大学理工学会誌) Volume: 17 Pages: 33-36
  • NAID: 110009591576
• [Journal Article] Tetradehydrodinaphtho[10]annulene and itstransformation into zethrene : A hithertounknown dehydroannulene and a forgottenaromatic hydrocarbon (2010)
  • Author(s): 梅田塁
  • Journal Title: Pure and Applied Chemistry 82(印刷中)
  • Peer Reviewed
• [Journal Article] Tetradehydrodinaphtho-[10]annulene : A Hitherto Unknown Dehydroannulene and a Viable Precursor to Stable Zethrene Derivatives (2009)
  • Author(s): Rui Umeda, Daijiro Hibi, Koji Miki, Yoshito Tobe
  • Journal Title: Org.Lett. 11 Pages: 4104-4106
  • Peer Reviewed
• [Journal Article] Tetradehydrodinaphtho[10]annulene : A Hitherto Unknown Dehydroannulene and a Viable Precursor to Stable Zethrene Derivatives (2009)
  • Author(s): 梅田塁
  • Journal Title: Organic Letters 11 Pages: 4104-4106
  • Peer Reviewed
• [Presentation] Synthesis and physical properties of zethrene derivatives (2010)
  • Author(s): Daijiro Hibi, Rui Umeda, 他2名
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, Hawaii, USA.
• [Presentation] ゼトレン誘導体の合成 (2010)
  • Author(s): 日比大二郎、梅田塁、他2名
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学本部キャンパス(大阪)
• [Presentation] ナフタルイミドが縮環した非対称なカルバゾール誘導体の合成と光学特性 (2010)
  • Author(s): 梅田塁
  • Organizer: 第27回有機合成化学セミナー
  • Place of Presentation: シーサイドホテル舞子ビラ神戸
• [Presentation] Synthesis and Photophysical Properties of Carbazoles and Dibenzofurans Having Naphthalimide Unit (2010)
  • Author(s): 梅田塁
  • Organizer: The Sixth International Symposium on Integrated Synthesis (ISIS-6)
  • Place of Presentation: Seaside Hotel Maiko Villa Kobe
• [Presentation] Synthesis and physical properties of zethrene derivatives (2010)
  • Author(s): 日比大治郎
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, Hawaii, USA
• [Presentation] Tetradehydro-dinaphtho[10]annulene : A Hitherto Unknown Dehydroannulene and a Viable Precursor to Stable Zethrene Derivatives (2009)
  • Author(s): Rui Umeda, 他3名
  • Organizer: The Eleventh International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-11)
  • Place of Presentation: Rihga Royal Hotel, Kyoto, Japan.
• [Presentation] Tetradehydrodinaphtho[10]annulene : A Hitherto Unknown Dehydroannulene and a Viable Precursor to Stable Zethrene Derivatives (2009)
  • Author(s): 梅田塁
  • Organizer: The 11th International KYOTO conference on New Aspests of Organic Chemistry
  • Place of Presentation: リーガロイヤルホテル京都(京都)