RSS-Feed abonnieren
DOI: 10.1055/s-2007-986646
A Bulky Silylene Generated under Mild Conditions: Its Application to the Synthesis of Organosilicon Compounds
Publikationsverlauf
Publikationsdatum:
12. September 2007 (online)
Abstract
By taking advantage of the bulky silylene Tbt(Mes)Si: (1) [Tbt = 2,4,6-(Me3Si)3C6H2, Mes = 2,4,6-Me3C6H2], generated under mild conditions from disilene Tbt(Mes)Si=Si(Mes)Tbt (2) or silylene-isocyanide complexes Tbt(Mes)SiCNAr (5), the synthesis of a variety of reactive silicon compounds, such as 2H-azasilirene, 2H-phosphasilirene, vinylsiliranes, silanone (intermediate) and silacyclic compounds containing chalcogens, was achieved. In addition, some unique reactivities of silylene 1, that is, [1+2] cycloaddition reactions to benzene and naphthalene, a double addition reaction with CS2 giving a disilacyclobutanethione derivative, and insertion reactions into B-H, B-F, B-Cl, and B-B bonds, were also revealed.
1 Introduction
2 Formation of a Bulky Silylene from the Corresponding Disilene
3 Application of the Bulky Silylene to the Synthesis of Reactive Silicon Compounds
3.1 Synthesis of Silylene-Isocyanide Complexes
3.2 Synthesis of a 2H-Azasilirene and a 2H-Phosphasilirene
3.3 Synthesis of Vinylsiliranes, the Intermediates in the Reaction with Dienes
3.4 Formation of a Silanone, a Silicon-Oxygen Double-Bond Compound
3.5 Synthesis of Silacyclic Compounds Containing Chalcogens
4 New Reactivities of the Bulky Silylene
4.1 [1+2] Cycloaddition to Aromatic Compounds
4.2 Reaction with Carbon Disulfide
4.3 Insertion into B-H, B-Cl, and B-B Bonds
5 Conclusion and Outlook
Key words
divalent silicon - reactive silicon compounds - steric hindrance - silylene - disilene
- 2
Hill NJ.West R. J. Organomet. Chem. 2004, 689: 4165 - 3
Kira M. J. Organomet. Chem. 2004, 689: 4475 - 4
Kira M.Ishida S.Iwamoto T. Chem. Rec. 2004, 4: 243 - 5
Gehrhus B.Lappert MF. J. Organomet. Chem. 2001, 617-618: 209 - 6
Tokitoh N.Okazaki R. Coord. Chem. Rev. 2000, 210: 251 - 7
Gaspar PP.West R. In The Chemistry of Organic Silicon Compounds Part 3, Vol. 2:Rappoport Z.Apeloig Y. Wiley & Sons; Chichester: 1998. p.2463-2567 - 8
Jutzi P.Kanne K.Krüger C. Angew. Chem., Int. Ed. Engl. 1986, 25: 164 - 9
Denk M.Lennon R.Hayashi R.West R.Belyakov AV.Verne HP.Haaland A.Wagner M.Metzler N. J. Am. Chem. Soc. 1994, 116: 2691 - 10
Kira M.Ishida S.Iwamoto T.Kabuto C. J. Am. Chem. Soc. 1999, 121: 9722 - 11
Driess M.Yao S.Brym M.van Wüllen C.Lentz D. J. Am. Chem. Soc. 2006, 128: 9628 - 12
So C.-W.Roesky HW.Magull J.Oswald RB. Angew. Chem. Int. Ed. 2006, 45: 3948 - 13
Jutzi P.Mix A.Neumann B.Rummel B.Stammler H.-G. Chem. Commun. 2006, 3519 - 14
Iwamoto T.Abe T.Kabuto C.Kira M. Chem. Commun. 2005, 4666 - 15
Abe T.Iwamoto T.Kabuto C.Kira M. J. Am. Chem. Soc. 2006, 128: 4228 - 16
Driess M.Yao S.Brym M.van Wüllen C. Angew. Chem. Int. Ed. 2006, 45: 6730 - 17
Okazaki R.Tokitoh N. Acc. Chem. Res. 2000, 33: 625 - 18
Tokitoh N.Okazaki R. Adv. Organomet. Chem. 2001, 47: 121 - 19
Tokitoh N. J. Organomet. Chem. 2000, 611: 217 - 20
Tokitoh N. Acc. Chem. Res. 2004, 37: 86 - 21
Okazaki R.Unno M.Inamoto N. Chem. Lett. 1987, 2293 - 22
Okazaki R.Tokitoh N.Matsumoto T. In Synthetic Methods of Organometallic and Inorganic Chemistry Vol. 2:Auner N.Klingebiel U. Thieme; New York: 1996. p.260-269 - 23
Tokitoh N.Suzuki H.Okazaki R.Ogawa K. J. Am. Chem. Soc. 1993, 115: 10428 - 24
Suzuki H.Tokitoh N.Okazaki R. Bull. Chem. Soc. Jpn. 1995, 68: 2471 - 25
Suzuki H.Tokitoh N.Ogawa K.Harada J.Ogawa K.Tomoda S.Goto M. Organometallics 1995, 14: 1016 - 26
Batcheller SA.Tsumuraya T.Tempkin O.Davis WM.Masamune S. J. Am. Chem. Soc. 1990, 112: 9394 - 27
Masamune S.Eriyama Y.Kawase T. Angew. Chem., Int. Ed. Engl. 1987, 26: 584 - 28
Tsutsui S.Sakamoto K.Kira M. J. Am. Chem. Soc. 1998, 120: 9955 - 29
Schmedake TA.Haaf M.Apeloig Y.Müller T.Bukalov S.West R. J. Am. Chem. Soc. 1999, 121: 9479 - 30
Tsutsui S.Tanaka H.Kwon E.Matsumoto S.Sakamoto K. Organometallics 2004, 23: 5659 - 31
Weidenbruch M.Brand-Roth B.Pohl S.Saak W. Angew. Chem., Int. Ed. Engl. 1990, 29: 90 - 32
Takeda N.Kajiwara T.Suzuki H.Okazaki R.Tokitoh N. Chem. Eur. J. 2003, 9: 3530 - 33
Takeda N.Suzuki H.Tokitoh N.Okazaki R.Nagase S. J. Am. Chem. Soc. 1997, 119: 1456 - 34
Weidenbruch M.Schäfer A.Peters K.von Schnering HG. J. Organomet. Chem. 1986, 314: 25 - 35
Schäfer A.Weidenbruch M.Saak W.Pohl S. Angew. Chem., Int. Ed. Engl. 1987, 26: 776 - 36
Tokitoh N.Suzuki H.Takeda N.Kajiwara T.Sasamori T.Okazaki R. Silicon Chem. 2002, 1: 313 - 37
Lei D.Hwang R.-J.Gaspar PP. J. Organomet. Chem. 1984, 271: 1 - 38
Gaspar PP.Hwang R.-J. J. Am. Chem. Soc. 1974, 96: 6198 - 39
Takeda N.Tokitoh N.Okazaki R. Chem. Lett. 2000, 622 - 40
Zhang S.Conlin RT. J. Am. Chem. Soc. 1991, 113: 4272 - 41
Gusel"nikov LE.Namekin NS. Chem. Rev. 1979, 79: 529 - 42
Raabe G.Michl J. Chem. Rev. 1985, 85: 419 - 43
Brook AG.Bains KM. Adv. Organomet. Chem. 1986, 25: 1 - 44
Tokitoh N.Okazaki R. In The Chemistry of Organic Silicon Compounds Vol. 2:Rappoport Z.Apeloig Y. John Wiley & Sons Ltd.; New York: 1998. p.1063-1103 - 45
Matsumoto T.Tokitoh N.Okazaki R. Chem. Commun. 1997, 1553 - 46
Takeda N.Tokitoh N.Okazaki R. Chem. Lett. 2000, 244 - 47
Takeda N.Tokitoh N.Okazaki R. Elemental Sulfur and Sulfur-Rich Compounds II, In Topics in Current Chemistry Vol. 231: Springer-Verlag; Berlin: 2003. p.153-202 - 48
Müller A.Diemann E. Adv. Inorg. Chem. 1987, 31: 89 - 49
Kolis JW. Coord. Chem. Rev. 1990, 105: 195 - 50
Draganjac M.Rauchfuss TB. Angew. Chem., Int. Ed. Engl. 1985, 24: 742 - 51
Tokitoh N.Suzuki H.Matsumoto T.Matsuhashi Y.Okazaki R.Goto M. J. Am. Chem. Soc. 1991, 113: 7047 - 52
Takeda N.Tanabe T.Tokitoh N. Bull. Chem. Soc. Jpn. 2006, 79: 1573 - 53
Tanabe T.Takeda N.Tokitoh N. Eur. J. Inorg. Chem. 2007, 1225 - 54
Schäfer A.Weidenbruch M.Peters K.von Schnering HG. Angew. Chem., Int. Ed. Engl. 1984, 23: 302 - 55
Sekiguchi A.West R. Organometallics 1986, 5: 1911 - 56
Suzuki H.Tokitoh N.Okazaki R. J. Am. Chem. Soc. 1994, 116: 11572 - 57
Kira M.Ishida S.Iwamoto T.Kabuto C. J. Am. Chem. Soc. 2002, 124: 3830 - 58
Jutzi P.Möhrke A. Angew. Chem., Int. Ed. Engl. 1989, 28: 762 - 59
Jutzi P.Eikenberg D.Möhrke A.Neumann B.Stammler H.-G. Organometallics 1996, 15: 753 - 60
Tokitoh N.Suzuki H.Okazaki R. Chem. Commun. 1996, 125 - 61
Metzler N.Denk M. Chem. Commun. 1996, 2657 - 62
Takeda N.Kajiwara T.Tokitoh N. Chem. Lett. 2001, 1076 - 63
Kajiwara T.Takeda N.Sasamori T.Tokitoh N. Organometallics 2004, 23: 4723 - 64
Kajiwara T.Takeda N.Sasamori T.Tokitoh N. Chem. Commun. 2004, 2218
References
Present address: Department of Chemistry and Chemical Biology, Graduate School of Engineering, Gunma University, 1-5-1 Tenjincho, Kiryu Gunma 376-8515, Japan.