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North, M., Science of Synthesis, (2002) 4, 499.
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The first silyl cyanide 1 (Scheme 1) was reported in 1941,[1] and during the following 30 years there was considerable debate as to whether these compounds existed as the silyl cyanide (R13SiCN) or silyl isocyanide (R13SiNC). Much of the chemical evidence favored the isocyanide form, for example reduction of silyl cyanides with lithium aluminum hydride leads to silylamines. Spectroscopic and structural studies, however, eventually determined that the cyanide and isocyanide forms were in equilibrium (Scheme 2), with the isocyanide form accounting for only around 5% of the population.[2–14] However, the term silyl isocyanide is still sometimes used instead of silyl cyanide. This section covers the synthesis of all such compounds, irrespective of whether they were originally reported as syntheses of the isocyanide or cyanide.
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References
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- 8.Meeeee-Meee, (8888) 88/8, 888.
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