Thermal Dissociation of Disilenes into Silylenes

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著者

    • SUZUKI Hiroyuki
    • Department of Chemistry, Graduate School of Science, The University of Tokyo
    • TOKITOH Norihiro
    • Department of Chemistry, Graduate School of Science, The University of Tokyo
    • OKAZAKI Renji
    • Department of Chemistry, Graduate School of Science, The University of Tokyo

抄録

Extremely hindered and stable disilenes (Tbt(Mes)Si=Si(Mes)Tbt {Tbt = 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl, Mes = 2,4,6-trimethylphenyl. (<i>Z</i>)-<b>1</b>: cis-isomer, (<i>E</i>)-<b>1</b>: trans-isomer}) underwent dissociation under very mild conditions (ca. 70 °C) into a divalent silicon species (Tbt(Mes)Si: (<b>2</b>)), which was trapped by methanol, triethylsilane, 2,3-dimethyl-1,3-butadiene, elemental sulfur, and elemental selenium to afford the corresponding adducts in good yields. Silylene <b>2</b> reacted with some carbon–carbon multiple-bond compounds to afford the corresponding [1 + 2] cycloadducts, among which the adduct with 3,3,6,6-tetramethylthiacyclohept-4-yne was established by an X-ray diffraction analysis. Silylene <b>2</b> also reacted with naphthalene and benzene to give the corresponding adducts, <b>15</b> and <b>17</b>, respectively, the molecular structures of which were confirmed by X-ray crystallographic analyses. The formation of <b>15</b> and <b>17</b> represents the first example of [1 + 2] cycloaddition of silylenes to aromatic compounds. The thermolysis of <b>15</b> and <b>17</b> regenerated silylene <b>2</b>, which was trapped with triethylsilane. A kinetic study of the thermal dissociation of <b>1</b> gave the activation parameters, which were compared with those for <i>E</i> <SUB></SUB> <i>Z</i> isomerization of previously reported disilenes.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(9), 2471-2481, 1995-09-15

    The Chemical Society of Japan

参考文献:  52件中 1-52件 を表示

  • <no title>

    WEST R.

    Pure Appl. Chem. 56, 163, 1984

    被引用文献4件

  • <no title>

    RAABE G.

    Chem. Rev. 85, 419, 1985

    被引用文献21件

  • <no title>

    WEST R.

    Angew. Chem., Int. Ed. Engl. 26, 1201, 1987

    被引用文献16件

  • <no title>

    WEIDENBRUCH M.

    Coord. Chem. Rev. 130, 275, 1994

    被引用文献1件

  • <no title>

    FINK M. J.

    J. Am. Chem. Soc. 105, 1070, 1983

    被引用文献3件

  • <no title>

    WEST R.

    J. Am. Chem. Soc. 107, 4942, 1985

    被引用文献1件

  • <no title>

    TAN R. P.

    Organometallics 10, 546, 1991

    被引用文献1件

  • <no title>

    FANTA A. D.

    Organometallics 12, 2177, 1993

    被引用文献2件

  • <no title>

    TOKITOH N.

    J.Am.Chem.Soc. 115, 10428, 1993

    被引用文献12件

  • <no title>

    SUZUKI H.

    Organometallics 14, 1016, 1995

    被引用文献6件

  • <no title>

    BATCHELLER S. A.

    Ph. D. Thesis, Massachusetts Institute of Technology, 1989

    被引用文献1件

  • <no title>

    MASAMUNE S.

    J. Am. Chem. Soc. 107, 6390, 1985

    被引用文献1件

  • <no title>

    BATCHELLER S. A.

    Angrew Chem. Int. Ed. Engl. 30, 902, 1991

    被引用文献1件

  • <no title>

    BARRAU J.

    Chem. Rev. 90, 283, 1990

    被引用文献17件

  • <no title>

    MICHALCZYK M. J.

    J. Am. Chem. Soc. 106, 821, 1984

    被引用文献1件

  • <no title>

    SHEPHERD B. D.

    Organometallics 8, 2664, 1989

    被引用文献1件

  • <no title>

    MICHALCZYK M. J.

    Organometallics 4, 826, 1985

    被引用文献1件

  • <no title>

    BROOKS P. R.

    J. Org. Chem. 59, 1365, 1994

    被引用文献1件

  • <no title>

    ISAACS N. S.

    Physical Organic Chemistry, 1-76, 1986

    被引用文献1件

  • <no title>

    KROGH-JESPERSEN K.

    J. Am. Chem. Soc. 107, 537, 1985

    被引用文献2件

  • <no title>

    GREV R. S.

    J.Am.Chem.Soc. 112, 9458, 1990

    被引用文献6件

  • <no title>

    GOLDBERG D. E.

    J.Chem.Soc., Dalton Trans. 1986, 2387

    被引用文献3件

  • <no title>

    TRINQUIER G.

    J.Am.Chem.Soc. 104, 4529, 1982

    被引用文献3件

  • <no title>

    MARQUEZ A.

    Chem. Phys. 138, 99, 1989

    被引用文献1件

  • <no title>

    GASPAR P. P.

    Reactive Intermekiates 1, 229-277, 1978

    被引用文献1件

  • <no title>

    GASPAR P. P.

    Reactive Intermekiates 2, 335-385, 1981

    被引用文献1件

  • <no title>

    GASPAR P. P.

    Reactive Intermekiates 3, 333-427, 1985

    被引用文献1件

  • <no title>

    ANDO W.

    J Am. Chem. Soc. 110, 3310, 1988

    被引用文献3件

  • <no title>

    ZHANG S.

    J. Am. Chem. Soc. 113, 4272, 1991

    被引用文献1件

  • <no title>

    PAE D. H.

    J. Am. Chem. Soc. 113, 1281, 1991

    被引用文献2件

  • <no title>

    BOUDJOUK P.

    Organometallics 10, 2095, 1991

    被引用文献3件

  • <no title>

    ISHIKAWA M.

    J. Organomet. Chem. 131, C15, 1977

    被引用文献2件

  • <no title>

    ISHIKAWA M.

    J. Organomet. Chem. 190, 117, 1980

    被引用文献1件

  • <no title>

    WEIDENBRUCH M.

    J. Organomet. Chem. 314, 25, 1986

    被引用文献1件

  • <no title>

    SHAFER A.

    Angew. Chem. Int. Ed. Engl. 26, 776, 1987

    被引用文献1件

  • <no title>

    WEIDENBRUCH M.

    Angew. Chem. Int. Ed. Engl. 29, 90, 1990

    被引用文献1件

  • <no title>

    DENK M.

    J. Chem. Soc., Chem. Commun. 1994, 33

    被引用文献6件

  • <no title>

    ISHIKAWA M.

    J. Organomet. Chem. 178, 105, 1979

    被引用文献3件

  • <no title>

    MASAMUNE S.

    Angew.Chem., Int.Ed.Engl. 26, 584, 1987

    被引用文献3件

  • <no title>

    MASAMUNE S.

    J. Am. Chem. Soc. 105, 7776, 1983

    被引用文献2件

  • <no title>

    HIROTSU K.

    J. Chem. Soc. Chem. Commun. 1982, 726

    被引用文献2件

  • <no title>

    SCHAFER A.

    Angew. Chem. Int. Ed. Engl. 23, 302, 1984

    被引用文献2件

  • <no title>

    SEKIGUCHI A.

    Organometallics 5, 1911, 1986

    被引用文献1件

  • <no title>

    AKASAKA T.

    J. Am. Chem. Soc. 115, 1605, 1993

    被引用文献13件

  • <no title>

    WULFMAN D. S.

    The Chemistry of Diazonium and Diazo Groups, 821-976, 1978

    被引用文献1件

  • <no title>

    STEWART J. J. P.

    J. Comput. Chem. 10, 221, 1989

    被引用文献27件

  • <no title>

    SHELDRICK G. M.

    SHELXS-86m Program for Crystal Structure Determination, 1986

    被引用文献1件

  • <no title>

    FAN H. -F.

    SAPI-90, Program for Crystal Structure Determination, 1990

    被引用文献1件

  • <no title>

    ZHANG S.

    J. Am. Chem. Soc. 113, 4278, 1991

    DOI 被引用文献1件

  • <no title>

    SUZUKI H.

    J. Am. Chem. Soc. 116, 11572, 1994

    DOI 被引用文献3件

  • <no title>

    NEFEDOV O. M.

    Izv. Akad. Nauk SSSR, Ser. Khim. 7, 1693, 1986

    被引用文献1件

  • <no title>

    BATCHELLER S. A.

    J. Am. Chem. Soc. 112, 9394, 1990

    DOI 被引用文献2件

各種コード

  • NII論文ID(NAID)
    10008892446
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092673
  • データ提供元
    CJP書誌  J-STAGE 
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