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Syntheses and Reactivities of Thiophenetriptycenesulfenic and selenenic acids

Research Project

Project/Area Number 09640624
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionSaitama University

Principal Investigator

ISHII Akihiko  Saitama University, Department of Chemistry, Associate Professor, 理学部, 助教授 (90193242)

Co-Investigator(Kenkyū-buntansha) SUGIHARA Yoshiaki  Saitama University, Department of Chemistry, Assistant Professor, 理学部, 助手 (00272279)
NAKAYAMA Juzo  Saitama University, Department of Chemistry, Professor, 理学部, 教授 (90092022)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 1998: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1997: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordssulfenic acid / selenenic acid / thiophenetriptycene / triptycene / selenoseleninate / dimethyldioxirane / oxidation / beta-elimination / セレニド / セレノール / セレノキシド / セレノセレニナ-ト
Research Abstract

Syntheses and reactivities of thiophenetriptycenesulfenic (Thtrip-SOH) and selenenic acids (Thtrip-SeOH) and triptycneneselenenic acid (Trip-SeOH) were investigated.
1. Attempted synthesis of Thtrip-SeOH The oxidation of Thtrip-Se-n-Bu with dimethyldioxirane (DMD) gave the corresponding selenoxide [Thtrip-Se(O)-n-Bu] . The thermal beta-elimination of the selenoxide yielded Thtrip-Se(O)Se-Thtrip, instead of the desired selenenic acid (ThtripSeOH). Thtrip-Se(O)Se-Thtrip is the first isolable selenoseleninates and the structure was determined by X-ray crystallography.
2. Synthesis of Trip-SeOH The oxidation of Trip-Se-n-Bu with DMD gave the corresponding selenoxide [Trip-Se(O)-n-Bu], the beta-elimination of which yielded the desired Trip-SeOH in a good yield. Trip-SeOH is the first isolable alkancselenenic acid and the structure was determined by X-ray crystallography.
3. Reactions of Trip-SeOH Heating a solution of Trip-SeOH in dichloromethane yielded the selenoseleninate, Trip-Se(O)Se-Trip. The dimerization was not accelerated by an acid. The treatment of Trip-Se(O)Se-Trip with Et^c_3N furnished a mixture of TripSe(O)SeTrip, Trip-SeSe-Trip, and Trip-SeO_2HEt_3N, the molar ratio of which was 1 : 1 : 1. Acid-catalized hydrolysis of TripSe(O)SeTrip gave TripSeOH quantitatively.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (3 results)

All Other

All Publications (3 results)

  • [Publications] Akihiko Ishii: "Preparation of a Selenenic Acid and Isolation of Selenoseleninates" Journal of Organic Chemistry. 64・4. 1084-1085 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Akihiko Ishii: "Preparation of a Selenenic Acid and Isolation of Selenoseleninates" Journal of Organic Chemistry. 64-4. 1084-1085 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Akihiko Ishii: "Preparation of a Selenenic Acid and Isolation of Selenoseleninates" Journal of Organic Chemistry. 64・4. 1084-1085 (1999)

    • Related Report
      1998 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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