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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 8
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Original Articles

An Improved Synthesis of Trimethylsilylmethyl Isocyanide

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Pages 865-869 | Published online: 19 Dec 2006

References

  • van Leusen , D. and van Leusen , A. M. 1984 . Recl. Trav. Chim. Pays-Bas , 103 : 41 For another interesting recent application of 3 see: G. Zinner and W. P. Fehlhammer, Angew. Chem., 97, 990 (1985) See, for example
  • West , R. and Gornowicz , G. A. 1970 . J. Organomet. Chem. , 25 : 385 this method was recently improved mainly by switching to another solvent (dimethoxymethane): R. Smith and T. Livinghouse, Synth. Comm., 14, 639 (1984).
  • Schuster , R. E. , Scott , J. E. and Casanova , J. 1973 . Org. Sunth., Coll. Vol. , V : 772 For warnings, see
  • Tsuge , O. , Kanemasa , S. and Matsuda , K. Chem. Lett. , 1983 1131 For related displacements see (using azide);
  • Schöllkopf , U. and Scholz , H. U. Synthesis , 1976 271 (using sodioacetamide).
  • Obrecht , R. , Herrmann , R. and Ugi , I. Synthesis , 1985 400
  • Foaming can be reduced by previously removing the mineral oil from sodium hydride with petroleum ether.
  • Since 2 is soluble in water, aqueous work up to remove DMF is not possible.
  • The NMR spectra clearly show a solvent and concentration dependent conformational equilibrium9, 10, 11 of s-trans-2 s-cis-2, with ca. 85% of s-trans-2 (i. e. s-Z-2) in CDCl3 (ca. 0.3 M), the signals of which are marked with an asterisk. (b) The chemical shifts are given with respect to the Me3Si of the molecule itself δ = 0.
  • Nakanishi , H. and Roberts , J. D. 1981 . Org. Magn. Res. , 15 : 7
  • Stewart , W. E. and Siddall , T. H. III . 1970 . Chem. Rev. , 70 : 517
  • LaPlanche , L. A. and Rogers , M. T. 1964 . J. Am. Chem. Soc. , 86 : 337

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