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Organic Synthesis Using Highly Strained Cyclopropenyl Cations

Research Project

Project/Area Number 05650885
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionOSAKA PREFECTURE UNIVERSITY

Principal Investigator

INOUE Hiroo  Osaka Prefecture University, College of Engineering Professor, 工学部, 教授 (10081316)

Co-Investigator(Kenkyū-buntansha) MATSUMURA Noboru  Osaka Prefecture Universty, College of Engineering, Research Associate, 工学部, 助手 (40125274)
HARUKI Eiichi  Osaks Prefecture Universty, College of Engineering, Lecture, 工学部, 講師 (90081322)
Project Period (FY) 1993 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1994: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1993: ¥1,700,000 (Direct Cost: ¥1,700,000)
KeywordsCycopropenyl Cation / Thiophene Derivatives / Pyrole Derivatives / alpha, beta-Unsaturated Carbonyl Compounds / シクロプロペニルカチオン類 / ピリジン誘導体 / 縮合ヘテロ環系化合物 / alpha,beta-不飽和カルボン酸類
Research Abstract

Tris (isopropylthio) cyclopropenylium perchlorate (1) is a useful three-carbon building block in organic synthesis. The results our obtained are summarized below.
1) Tris (isopropyltho) cyclopropenylium perchlorate (1) reacts with potassium dithiocarbamates to give thiophene derivatives in good yield.
2) Tris (isopropylthio) cyclopropenylium perchlorate (1) reacts with sodium arylsulfinates in dry acetonitlile and benzene under reflux to give arylsulfinylpropenethioates in good yield.
accompanied by the formation of arylsulfonylallenes, through cyclopropene intermediates and then vinylcarbene,
3) The reaction of tris (isopropylthio) cyclopropenylium perchlorate (1) with alpha-Lithiated tosylmethyl, benzyl and benzoylmethyl isocyanides in dry tetrahydrofuran gave the pyridine deribatives, respectively.

Report

(3 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • Research Products

    (3 results)

All Other

All Publications (3 results)

  • [Publications] Hideo Kojima: "A New Route to Pyridine Derivatives by the Reaction of Tris(isopropylthio)-cyclopropenylium Perchlorate with alpha-Lithiated Isocyanides" J.Heterocyclic Chemistry. 30. 1691-1692 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Hideo Kojima: "Intramolecular Transfer of Sulfonyl Oxygen to Vinylcarbene Generated in the Reaction of Tris(isopropylthio)cyclopropenyl Cation with Arylsulfinate Salts" J.Chem.Soc.,Chem.Commun. 1674-1676 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Hideo Kojima: "New Organic Reactions using Cyclopropenyl Cations as a Three-carbon Building Block" 3rd Tohwa Univ.Int.Symp.Proc.235 (1993)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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