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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 23
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Original Articles

A Convenient Large Scale Synthesis of 1, 1-Diphenyl-1 -silacyclopent-3-ene

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Pages 3855-3861 | Received 19 May 1995, Published online: 23 Sep 2006

References

  • Lesbre , M. , Manuel , G. , Mazerolles , P. and Cauquy , G. 1972 . J. Organomet. Chem. , 40 : 14
  • Manuel , G. , Mazerolles , P. and Darbon , J. M. 1973 . J. Organomet. Chem. , 59 : 7
  • Manuel , G. , Mazerolles , P. , Lesbre , M. and Pradel , J. P. 1973 . J. Organomet. Chem. , 61 : 147
  • Manuel , G. , Cauquy , G. and Mazerolles , P. 1974 . Syn. Inorg. Met. Org. Chem. , 4 : 143
  • Manuel , G. , Mazerolles , P. and Grill , J. 1976 . J. Organomet. Chem. , 122 : 335
  • Manuel , G. , Bertrand , G. and Mazerolles , P. 1978 . J. Organomet. Chem. , 146 : 7
  • Guimon , C. , Pfister-Guillouzo , G. , Manuel , G. and Mazerolles , P. 1978 . J. Organomet. Chem. , 149 : 149
  • Manuel , G. , Bertrand , G. and Anba , F. E. 1983 . Organometallics , 2 : 391
  • Manuel , G. , Faucher , A. and Mazerolles , P. 1987 . J. Organomet. Chem. , 327 : 25
  • Zhang , X. , Weber , W. P. , Horvath , K. F. , Chan , T. H. and Manuel , G. 1988 . Macromolecules , 21 : 1563
  • Zhang , X. , Weber , W. P. , Horvath , R. F. , Chan , T. H. and Manuel , G. 1990 . Adv. in Chemistry Series Edited by: Zeigler , J. M. and Fearon , Gordon . 679 American Chemical Society .
  • Park , Y. T. , Manuel , G. , Bau , R. and Weber , W. P. 1991 . Organometallics , 10 : 1586
  • Manuel , G. and Boukkerroub , R. 1993 . J. Organomet. Chem. , 447 : 165
  • Boukkerrou , R. , Manuel , G. , Mignani , S. and Damour , D. 1994 . J. Organomet. Chem. , 484 : 119
  • Damour , D. and Mignani , S. 1994 . Synt. Comm. , 24 : 2017
  • Mignani , S. and Damour , D. French Patent Applications: FR 2689892, FR 2689893. and FR 2689894 .
  • Chernyshev , E. A. , Komalenkova , N. G. , Bashkirova , S. A. and Sokolov , V. V. 1978 . Zh. Obshch. Kim. , 48 ( 4 ) : 830 Condensation of dichlorosilylene (genered in situ by the pyrolysis of Cl3SiSiCl3 at 500°C) with buta-1, 3-diene giving 1, 1-dichloro-1-silacyclopent-3-ene followed by the addition of phenylmagnesium bromide affording 1 in 59% overall yield was reported by
  • C.A. , 89 043589
  • Richter , W. J. 1982 . Synthesis , 12 : 1102 Condensation of dichlorodiphenylsilane to the complex magnesium-buta-1, 3-diene affording 1 in 77% yield was reported by A violent decomposition was observed by us during the preparation of magnesium-buta-1, 3-diene complex which consequently precluded its utilization as a large scale starting material
  • Manuel , G. , Mazerolles , P. , Lesbre , M. and Pradel , J. P. 1973 . J. Organomet. Chem. , 61 : 147 Condensation of dichlorodiphenylsilane with buta-1, 3-diene in presence of magnesium in pure HMPT to give 1 in 30% yield was described by
  • Manuel , G. , Mazerolles , P. and Florence , J. C. 1971 . J. Organomet. Chem. , 30 : 5 Condensation of diphenyldichlorosilane with the cis-2-butene-1, 4-dimagnesium dibromide (genered in situ from cis-1, 4-dibromo-2-butene) in diethylether in 60% yield was described by
  • Manuel , G. , Mazerolles , P. and Cauquy , G. 1974 . Syn. Inorg. Met. Org. Chem. , 4 ( 2 ) : 133
  • Gaspar , P. P. 1978 . “Silylenes” . In Reactive Intermediates , Edited by: Jones , M. Moss Jr. and Moss , R. A. Vol. 1 , 229 – 277 . New York : Wiley . The generation of silylenes by interaction of alkali metals with dihalosilanes has been well documented; see for example: and references cited therein
  • Manuel , G. and Weber , W. P. 1988 . “1, 1-Dimethyl-1-silacyclopent-3-ene” . In Organometallic Synthesis , Edited by: King , R. B. and Eisch , J. J. Vol. 4 , 477 – 482 . New York : Elsevier . and references cited therein
  • Gusel'nikov , E. , Volnina , E. A. and Kanevskii , A. B. 1989 . Zh. Obshch. Khim. , 59 ( 10 ) : 2397
  • 1990 . Engl. Transl. , 2146
  • Clarke , M. P. and Davidson , L. M. T. 1988 . J. Chem. Soc., Chem. Commun. , : 241
  • Clarke , M. P. , Davidson , L. M. T. and Dillon , M. P. 1988 . J. Chem. Soc., Chem. Commun. , : 1139 The mechanism of addition of diphenylsilylene to buta-1, 3-diene (1, 2-addition followed by a 1, 3-silyl shift) giving the compound 1 is probably identical to this addition of dimethylsilylene to dienes. For further references see:
  • Clarke , M. P. , Davidson , L. M. T. and Dillon , M. P. 1988 . J. Chem. Soc., Chem. Commun. , : 1251 and references therein
  • Filleux-Blanchard , M. L. , An , Nguyen-Dinh and Manuel , G. 1977 . J. Organomet. Chem. , 137 : 11
  • Filleux-Blanchard , M. L. , An , Nguyen-Dinh and Manuel , G. 1978 . Organic Magnetic Resonance , 11 : 150

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