• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

PREPARATION OF OLEFINS AND SMALL RING COMPOUNDS BY THE USE OF 2-SELENOAZAAROMATIC COMPOUNDS

Research Project

Project/Area Number 03640462
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionAOYAMA GAKUIN UNIVERSITY

Principal Investigator

OYO Mitsunobu  AOYAMA GAKUIN UNIVERSITY, COLLEGE OF SCIENCE AND ENGINEERING PROFESSOR OF CHEMISTRY, 理工学部, 教授 (90082792)

Project Period (FY) 1991 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1992: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1991: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsOrganoselenium Compound / Olefin / Selenetane / Stereospecific Reaction / 有機セレン化合物 / オレフィン / セレネタン / 立体特異的反応 / 2ーセレノアザ芳香族化合物 / 1、4ージエン / Se→Oアザ芳香核転位
Research Abstract

1) Reaction of 2-(2-oxoalkylseleno)benzazoles 1(X = S, O, N-Me) with allylic Grignard reagents in the presence of BF_3・OEt_2 afforded the corresponding selenoalcohols 2(X = S, O, N-Me ; R^2 = H or Me)which were converted into 1,4-dienes 3 by treatment with bases.
2) The hydride reduction of selenoketones1(X = S,O)gave selenoalcohols4. Benzoxazole derivatives were found to afford syn-selenoalcohols(syn-4) in preference to anti-isomers, While reverse was found for benzthiazole derivatives. On treatment with base, anti-selenoalcohols(anti-4)and syn-selenoalcohols(syn-4)respectively gave E-olefins(E-5)and Z-olefins(Z-5).
3)The reaction of 2-(benzoylalkylseleno)azole 1(X = S or O ; R = R^1 = Ph)with alcohols(R^2OH)in the presence of tributylphosphine gave 2-alkylseleno-azoles 6 in moderate to good yields.
4) When 2-(3-hydroxyalkylseleno)benzoxazoles 7 were treated with KH, selenetanes 8 or spiro compounds 9, the precursor of selenetane, were isolated, depending on the reaction conditions.

Report

(3 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] 有機セレン化合物:

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Shibata,H.Shiono,and O.Mitsunobu: "Preparation of 1,4-Dienes from 2-(2-Hydroxyalkylseleno)-benzothiazoles by the Reaction Involving Se→O Aza-aromatic Ring Rearrangement" Chem.Lett.661-664 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Shibata and O.Mitsunobu: "Preparation of 1,4-Dienes from 2-(2-Hydroxyalkylseleno)-benzothiazoles by the Reaction Involving Se→O Azaaromatic Ring Rearrangement" Bull.Chem.Soc.Jpn.65. 3163-3173 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Shibata and O.Mitsunobu: "Preparation of 2-(Alkylseleno)benzothiazoles.Direct Incor-poration of the Alkyl Group of Alcohols into Benzo-thiazolylseleno Residue" Chem.Lett.549-552 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Shibata, H.Shiono, and O.Mitsunobu: "Preparation of 1,4-Dienes from2-(2-Hydroxy-alkylseleno)benzothiazoles by the Reaction Involving Se*O Aza-aromatic Ring Rearrangement" Chem.Lett.No.4. 661-664 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Shibata and O.Mitsunobu: "Preparation of 1,4-Dienes from2-(2-Hydroxyalkylseleno)- benzothiazoles by the Reaction Involving Se*O Azaaromatic Ring Rearrangement" Bull.Chem.Soc. Jpn., 65, No.11. 3163-3173 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Shibata and O.Mitsunobu: "Preparation of2-(Alkylseleno)benzothiazoles. Direct Incorporation of the Alkyl Group of Alcohols into Benzothiazolylseleno Residue" Chem.Lett. No.3. 549-552 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Shibata and O.Mitsunobu: "Preparation of 1,4-Dienes from 2-(2-Hydroxyalkylseleno)-benzothiazoles by the Reaction Involving Se→O Azaasromatic Ring Rearrangement" Bull.Chem.Soc.Jpn.65. 3163-3173 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Shibata and O.Mitsunobu: "Preparation of 2-(Alkylseleno)benzothiazoles.Direct Incorporation of the Alkyl Group of Alcohols into Benzothiazolylseleno Residue" Chem.Lett.549-552 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Shibata,H.Shiono,and O.Mitsunobu: "Preparation of 1,4ーDienes from 2ー(2ーHyroxyalkylseleno)benzothiazoles by the Reaction involving Se→O Azaーaromatic Ring Rearrangement" Chem.Lett.661-664 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] T.Sakamaki and O.Mitsunobu: "Reaction of 2ー(Hydroxyalkylseleno)benzimidazoles with Base.Preparation of Olefins,Cyclic Ethers and Selenetanes"

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Sakano and O.Mitsunobu: "Reaction of 2ー(2ーOxoalkylseleno)benzoxazoles with Organometalic Reagents and with Hydrides"

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Shibata,T.Motegi,and O.Mitsunobu: "A Novel Procedure for the Preparation of 2ー(Hydroxyalkylseleno)benzothizaoles"

    • Related Report
      1991 Annual Research Report

URL: 

Published: 1991-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi