Preparation of polycyclic hetero-annulenes by intramolecular triple metathesis

• Project/Area Number: 26620027
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Shizuoka University
• Principal Investigator: Sakamoto Kenkichi 静岡大学, 理学部, 教授 (50187035)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2014: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 分子内閉環メタセシス / 縮合多環ヘテロアヌレン / シクロブテニルシラン / グラブス触媒 / シュロック触媒 / ヘテロフェナレン / 1-シクロブテニルリチウム / 1-シクロブテニルシラン / シャピロ反応

Outline of Final Research Achievements

The aim of this project is development of novel synthetic method of tricyclic heteroatom-centered annulenes by intramolecular triple ring-closing metathesis. Tris(2-hexa-1,5-dieneyl)silanes and tris(1-cyclobutenyl)silanes are employed as promising precursors of silaphenalene derivatives via sequential intramolecular metathesis.
The metathesis of these compounds in the presence of various Grubbs catalysts is now in progress.

Research Products

• [Journal Article] Photoracemization of Blestriarene C and Its Analogs (2015)
  • Author(s): Natori, K.; Iwayama, T.; Yamabe, O.; Kitamoto, Y.; Ikeda, H.; Sakamoto, K.; Hattori, T.; Miyano, S.
  • Journal Title: Chirality Volume: 27 Issue: 8 Pages: 479-486
  • DOI: 10.1002/chir.22447
  • Peer Reviewed / Acknowledgement Compliant
• [Presentation] シクロプロペンノンの異常なPetersonおよびWittig反応 (2016)
  • Author(s): 坂本 健吉,埴谷 開人
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学京田辺キャンパス （京都府京田辺市）
  • Year and Date: 2016-03-24
• [Presentation] アルキル置換オリゴシレタンの合成と性質 (2016)
  • Author(s): 坂本 健吉,楊 文博
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学京田辺キャンパス （京都府京田辺市）
  • Year and Date: 2016-03-24
• [Presentation] ジキノニルジシラン誘導体の合成と反応 (2016)
  • Author(s): 坂本 健吉,川崎 貴之
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学京田辺キャンパス （京都府京田辺市）
  • Year and Date: 2016-03-24
• [Presentation] トリシリルシクロドデカトリエンの合成と反応 (2016)
  • Author(s): 坂本 健吉,岡 祥平
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学京田辺キャンパス（京都府京田辺市）
  • Year and Date: 2016-03-24
• [Presentation] 1-シクロブテニルシランの合成と反応 (2016)
  • Author(s): 坂本 健吉,杉野 拓実
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学京田辺キャンパス （京都府京田辺市）
  • Year and Date: 2016-03-24
• [Presentation] Synthesis, properties, and reactions of quinone-fused siloles (2015)
  • Author(s): 坂本 健吉,川﨑 貴之,河部 千香,渡辺 貴大
  • Organizer: 環太平洋国際化学会議2015
  • Place of Presentation: 米国ハワイ州ホノルル
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Preparation and reactions of 1-cyclobutenylsilanes (2015)
  • Author(s): 坂本 健吉,杉野 拓実
  • Organizer: 環太平洋国際化学会議2015
  • Place of Presentation: 米国ハワイ州ホノルル
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Synthesis, properties, and reactions of oligosiletanes (2015)
  • Author(s): 坂本 健吉,楊 文博
  • Organizer: 環太平洋国際化学会議2015
  • Place of Presentation: 米国ハワイ州ホノルル
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Preparation and some reactions of trilithiocyclododecatriene (2015)
  • Author(s): 坂本 健吉,岡 祥平
  • Organizer: 環太平洋国際化学会議2015
  • Place of Presentation: 米国ハワイ州ホノルル
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Reactions of di-tert-butylcyclopropenone with Peterson and Wittig reagents (2015)
  • Author(s): 坂本 健吉,埴谷 開人
  • Organizer: 環太平洋国際化学会議2015
  • Place of Presentation: 米国ハワイ州ホノルル
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Preparation and reactions of oxygen-functionalized dibenzodisilacyclohexadiene (2015)
  • Author(s): 坂本 健吉,川崎 貴之
  • Organizer: 環太平洋国際化学会議2015
  • Place of Presentation: 米国ハワイ州ホノルル
  • Year and Date: 2015-12-15
  • Int'l Joint Research