Science of Synthesis

Suginome, M.; Ito, Y., Science of Synthesis, (2004) 19, 520.

General Introduction

There are fewer examples of isocyanides that contain isocyano—heteroatom bonds compared to carbon-bound isocyanides. A major reason for this seems to be the instability of heteroatom-bound isocyanides. Among the heteroatom-bound isocyanides, N-bound isocyanides have been studied extensively, although the majority of these still suffer from decomposition, even at ambient temperatures. N-Isocyanodialkylamines ‌231‌ (R1 = R2 = alkyl) bearing relatively bulky substituents can be isolated in a pure state and can be handled at ambient temperatures (‌Scheme 124‌).[‌275‌] A series of N-monosubstituted derivatives (‌231‌, R2 = H) can be isolated at low temperatures, but these are prone to decomposition on even a slight elevation in temperature.[‌276‌] The presence of aryl groups on the amino nitrogen atoms of such compounds accelerates the isocyanide–nitrile rearrangement, making their isolation difficult.[‌276‌]

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References