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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 7
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Original Articles

An Improved Synthesis of Trimethylsilylmethyl Isocyanide and Some of Its Reactions with Nucleophiles

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Pages 639-646 | Published online: 05 Dec 2006

References

  • Smith , R. and Livinghouse , T. 1983 . J. Org. Chem. , 48 : 1554
  • Vedejs , E. and Martinez , G. R. 1980 . J. Am. Chem. Soc. , 102 : 7993
  • Livinghouse , T. and Smith , R. 1983 . J. Chem., Soc., Chem. Commun. , : 210
  • West , R. and Gornowitz , G. A. 1970 . J. Organometal, Chem. , 25 : 385
  • The substitution of alternate low boiling ether solvents (e.g. diethyl ether) lead to inferior yields of the isocyanide 3. In the case of diethyl ether, the low yield of 3. is a direct consequence of the inability to metalate methyl isocyanide in this solvent at -78°C
  • The execution of this preparation on a smaller scale (e.g. 50mmol) allows yields of 70%–85% to be obtained
  • Attempts to utilize other copper catalysts (e.g. Cu, Cu20, and Cu(acac)2) to effect the insertion reaction between amines and the isocyanide 3. lead to a much greater proportion of products arising from desilylation of 3

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