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2,6-Dimethoxyphenyl Derivatives of a Variety of Elements

Research Project

Project/Area Number 08455429
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionTOTTORI UNIVERSITY

Principal Investigator

WADA Masanori  Department of Materials Sciences, Faculty of Engineering, Tottori University (Professor), 工学部・物理工学科, 教授 (30029053)

Co-Investigator(Kenkyū-buntansha) HAYASE Shuichi  Department of Materials Sciences, Faculty of Engineering, Tottori University (Re, 工学部, 助手 (50238143)
ERABI Tatsuo  Department of Materials Sciences, Faculty of Engineering, Tottori University (As, 工学部, 助教授 (60032025)
夏目 聡子  鳥取大学, 工学部, 教務職員 (50273884)
Project Period (FY) 1996 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥4,700,000 (Direct Cost: ¥4,700,000)
Fiscal Year 1998: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1997: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1996: ¥2,900,000 (Direct Cost: ¥2,900,000)
Keywords2,4,6-Trimethoxyphenyl / 2,6-Dimethoxyphenyl / Carbenium / Ferrocenyl / Organosulfur / Organoselenium / Organotellurium / 9-Phenylxanthenylium / 2,4,6-トリメトキシフェニル基 / 2,6-ジメトキシフェニル基 / ジアリールカルベニウム / フェロセニルカルベニウム / 2,4,6-トリメトキシフェニル / トリアリールカルベニウム塩 / ジアリールカルベニウム塩 / 4-メチレン-2,5-シクロヘキサジエノン誘導体 / 2,6-ジメトキシベンゼンチオール / トリアリール金属 / 金属酸化物 / 金属チオラート / 2,6-ジメトキシフェニル / アリール基転移 / カルベニウムイオン / 1,4-シクロヘキサジエン
Research Abstract

Abbr.phi^a= 2,4,6-(MeO)3C6H2- ; phi^a= 2,6-(MeO)2C6H3-.
1. phi^aCOH reacted with a slight excess of acids to give carbenium salts [phi^a_3]X.Neutralization of 1 M acidic solution of [phi^a_3] resulted in the substitution of one of the para-methoxy groups. [phi^a_2]CHOH also reacted with perchioric acid to give [phi^a_2]CH_4, which was reduced in alcohols to give phi^a_2CH_<2->.
2. phi^a_2CHOH reacted with acetone in the presence of catalytic amount of an acid to give phi^a_2CHCH_2COme. Me. Analogous reactions were observed with diethyl ketone, methyl phenyl ketone, propanal, and butanal. phi^a_2CHOH was reduced in alcohols or THF to give phi^a_2CH_2.
3. Fc-CHphi^aOH [Fc= ferrocenyl group] reacted with a slight excess of an acid to give [Fc-CHphi^a]X(pKr+=3.0). The salt was reduced in 2-propanol to give Fc-CH_2phi^a and reacted with phi^b-CHphi^a_2,
4. On treatment of p-HOcphi^b_2C_6H_4CAphi^bOH(Ar=phi^b, 4-MeOC_6, 4-MeOC_6H_4) with an acid, the Ar-group migrated onto the phenylene group.
5. The reactivities of l, 8-dlrnethoxy-9-phenylxanthen-9-ol were compared with those of without difficulty.
6. Novel method of preparation of triarymetals MAr_3(M=As, Sb, Bi) was developed. It is composed of the preparation of M(Sphi^b)_3 from metal oxides and phi^bSH and the reaction with LiAr. Both phiSH and M(Sphi^b)_3 are crystalline, and they can be handled without difficulty.
7. Nucleophilic reaction rates of phi^b_2E increased in the order E= S <Se <Te, which were compared with those of phi^b_3 (M= P > As> Sb). The rates of phi^b_2EO increased in the order E= S <Se <Te).

Report

(4 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • 1996 Annual Research Report
  • Research Products

    (21 results)

All Other

All Publications (21 results)

  • [Publications] Masanori Wada: "Formation of 3-Methylene-1, 4-cyclohexadienes from α, α, α′, α′-Tetraaryl-1,4-benzenedimethanols by the Intramolecular Migration of an Aryl Group" Bull.Chem.Soc.Jpn.70(6). 1413-1420 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Masanori Wada: "Unusual Stabilities and Reactivities of Tris-and Bis(2, 4, 6-trimethoxyphenyl)carbenium Salts" Bull.Chem.Soc.Jpn.70(1). 2737-2741 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Masanori Wada: "Two-step synthesis of triarylmetals (As, Sb, Bi)starting from the metal oxides and 2, 6-dimethoxybenzenethiol" J.Organometal.Chem.548. 223-227 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Masanori Wada: "Reactions of Bis(2, 6-dimethoxyphenyl)methanol in Common Organic Solvents in the Presence of an Acid" Bull.Chem.Soc.Jpn.71(7). 1667-1672 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Satoko Natsume: "Stability and reactivity of ferrocenyl(2, 4, 6-trimethoxyphenyl)carbenium salts" J.Organometal.Chem.574. 86-93 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Masanori Wada: "Bis(2, 6-dimethoxyphenyl)sulfide, selenide and telluride, and their derivatives" J.Organormetal.Chem.(印刷中). (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Masanori Wada: "Reactions of 1, 8-Dimethoxy-9-phenylxanthen-9-ol in the Presence of an Acid, and its Basicity" Bull.Chem.Soc.Jpn.72(印刷中). (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] WADA,Masanori: "Formation of 3-Methylene-1,4-cyclohexadienes from alpha, alpha, alpha', alpha'-Tetraaryl-1,4-benzenedimethanols by the Intramolecular Migration of an Aryl Group" Bull.Chem.Soc.Jpn.Vo.70 (6). 1413-1420 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] WADA,Masanori: "Unusual Stabilities and Reactivities of Tris-and Bis (2,4,6-trimethoxyphenyl) carbenium Salts" Bull.Chem.Soc.Jpn.Vol.70 (11). 2737-2741 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] WADA,Masanori: "Two-step synthesis of triarylmetals (As, Sb, Bi) starting from the metal oxides and 2,6-dimethoxybenzenethiol" J.Organometal.Chem.Vol.548. 223-227 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] WADA,Masanori: "Reactions of Bis (2,6-dimethoxyphenyl) methanol in Common Organic Solvents in the Presence of an Acid" Bull.Chem.Soc.Jpn.Vol.71 (7). 1667-1672 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] NATSUME,Satoko: "Stability and reactivity of ferrocenyl (2,4,6-trimethoxyphenyl) carbenium salts" J.Organometal.Chem.Vol.574. 86-93 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] WADA,Masanori: "Bis (2,6-dimethoxyphenyl) sulfide, selenide and telluride, and their derivatives" J.Organometal.Chem.(in press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] WADA,Masanori: "Reactions of 1,8-Dimethoxy-9-phenylxanthen-9-ol in the Presence of an Acid, and its Basicity" Bull.Chem.Soc.Jpn.Vol.72 (in press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Masanori Wada,^* Hideki Konishi, Takanori Kai, Hiroshi Takeuchi, Satoko Natsume,and Tatsuo Erabi: "Reactions of Bis (2,6-dimethoxyphenyl) methanolin Common Organic Solvents in the Presence of an Acid" Bull.Chem.Soc.Jpn. 71. 1667-1672 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Satoko Natsume, Hideaki Kurihara, Takuya Yamaguchi, Tatsuo Erabi,and Masanori Wada^*: "Stability and reactivity of ferrocenyl (2,4,6-trimethoxyphenyl) carbenium salts" J.Organomet.Chem.574. 86-93 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masanori Wada,^* Shin-ichi Nobuki, Yoshinori Tenkyuu, Satoko Natsume, Masahiro Asahara, Tatsuo Erabi: "Bis (2,6-dimethoxyphenyl) sulfide,selenide and telluride,and their derivatives" J.Organomet.Chem.印刷中 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masanori Wada,^* Katsuhiko Kirishima, Yuichi Oki, Masafumi Miyamoto, Masahiro Asahara,and Tatsuo Erabi: "Reactions of 1,8-Dimethoxy-9-phenylxanthen-9-ol in the Presence of an Acid,and its Basicity" Bull.Chem.Soc.Jpn.72(印刷中). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Wada, H.Konishi, K.Kirishima, H.Takeuchi, S.Natsume, and T.Erabi: "Unusual Stabilities and Reactivities of Tris-and Bis (2,4,6-trimethoxyphenyl) carbenium Salts" Bull.Chem.Soc.Jpn.70(11). 2737-2741 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Wada, S.Natsume, S.Suzuki, A.Uo, M.Nakamura, S.Hayase, and T.Erabi: "Two-step synthesls of trlarylmetals (As,Sb,Bi) starting from the metal oxides and 2,6-dimethoxybenzenethiol" J.Organometal.chem.548. 223-227 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Wada,W.Wei,K.Kirishima,S.Natsume,and T.Erabi: "Formation of 3-Methylene-1,4-cyclohexadienes from α,α,α′,α′-Tetraaryl-1,4-benzendimethanols by the Intramolecular Migration of an Aryl Group" Bull.Chem.Soc.Jpn.70巻(印刷中). (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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