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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 4
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Original Articles

Preparation of a Trans α,β-Epoxysilane by Selective Pyrolysis

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Pages 333-339 | Received 26 Oct 1978, Published online: 05 Dec 2006

References

  • 2005 . To whom correspondence should be addressed at the Department of Chemistry , 9 Washington, D. C. : Howard University .
  • Hudrlik , P. F. 1976 . “New Applications of Organometallic Reagents in Organic Synthesis,” , Edited by: Seyferth , D. 127 – 159 . Amsterdam : Elsevier .
  • Chan , T.-H . 1977 . Accounts Chem. Res. , 10 : 442 – 448 .
  • Colvin , E. W. 1978 . Chem. Soc. Rev. , 7 : 15 – 64 .
  • Stork , G. and Colvin , E. 1971 . J. Am. Chem. Soc. , 93 : 2080
  • Stork , G. and Jung , M. E. 1974 . J. Am. Chem. Soc. , 96 : 3682
  • Fristad , W. E. , Bailey , T. R. and Paquette , L. A. 1978 . J. Org. Chem. , 43 : 1620
  • Hudrlik , P. F. , Misra , R. N. , Withers , G. P. , Hudrlik , A. M. , Rona , R. J. and Arcoleo , J. P. 1976 . Tetrahedron Lett. , : 1453 see also
  • Obayashi , M. , Utimoto , K. and Nozaki , H. 1977 . Tetrahedron Lett. , : 1807
  • Hudrlik , P. F. , Peterson , D. and Rona , R. J. 1975 . J. Org. Chem. , 40 : 2263
  • Hudrlik , P. F. , Hudrlik , A. M. , Rona , R. J. , Misra , R. N. and Withers , G. P. 1977 . J. Am. Chem. Soc. , 99 : 1993
  • Hudrlik , P. F. , Rona , R. J. , Schwartz , R. H. and Hogan , J. C. 1977 . 11th Organosilicon Symposium . March 19 1977 , Kansas City, Missouri.
  • Rona , R. J. 1978 . New Brunswick, New Jersey : Rutgers University . Ph. D. Thesis
  • Burford , C. , Cooke , F. , Ehlinger , E. and Magnus , P. 1977 . J. Am. Chem. Soc. , 99 : 4536 For a new method, see
  • Benkeser , R. A. , Burrous , M. L. , Nelson , L. E. and Swisher , J. V. 1961 . J. Am. Chem. Soc. , 83 : 4385
  • Ryan , J. W. and Speier , J. L. 1966 . J. Org. Chem. , 31 : 2698
  • Lukevics , E. , Belyakova , Z. V. , Pomerantseva , M. G. and Voronkov , M. G. 1977 . J. Organometal. Chem. Library , 5 : 1 – 179 . for a review, see
  • Benkeser , R. A. , Cunico , R. F. , Dunny , S. , Jones , P. R. and Nerlekar , P. G. 1967 . J. Org. Chem. , 32 : 2634 For example, see J. Yoshida, K. Tamao, M. Takahashi, and M. Kumada (Tetrahedron Lett., 2161(1978)) have recently reported that the regiosel-ectivity of chloroplatinic acid-catalyzed hydrosilylation of terminal acetylenes with Cl3SiH is improved to 95% at 5°C
  • Hudrlik , P. F. , Wan , C.-N and Withers , G. P. 1976 . Tetrahedron Lett. , : 1449
  • Bassindale , A. R. , Brook , A. G. , Chen , P. and Lennon , J. 1975 . J. Organometal. Chem. , 94 : C21
  • Eisch , J. J. and Galle , J. E. 1976 . J. Org. Chem. , 41 : 2615 Additional pyrolyses of α,β–epoxysilanes have been reported in the following papers M. Lesbre, G. Bertrand, G. Manuel, and P. Mazerolles, C. R. Acad. Sci. Paris, Ser. C, 284, 709(1977)
  • Vapor phase chromatographic (VPC) analyses were performed on a Varian model 90-P instrument using helium as the carrier gas, using a 20 ft × 0.25 in. aluminum column packed with 25% Car-bowax 20M on Chromosorb W
  • Neumann , H. and Seebach , D. 1976 . Tetrahedron Lett. , : 4839 We have also prepared the trans vinyl si lane 1b6b from the corresponding vinyl iodide by treatment with t-BuLi followed by Me3SiCl The vinylsilane from that procedure was contaminated with 1–2% of the cis isomer
  • CHCl3 (δ 7.25) was used as the internal reference
  • From a separate but similar experiment (on a smaller scale)

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