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Subramanian, L. R., Science of Synthesis, (2004) 19, 163.
General Introduction
Organometallic compounds are very reactive species which find widespread use as reagents in C—C bond-forming reactions. The reaction of organometallics with recognized nitrile transfer reagents is certainly an attractive method for the production of nitriles; however, reports of such chemistry are few. Highly volatile and toxic cyanogen chloride,[1,2] cyanogen bromide,[3] and cyanogen[4,5] have all been used in earlier work to obtain nitriles from organometallics. The reaction of Grignard reagents or vinyl- and alkynyllithiums with phenyl cyanate[6,7] has also been reported to afford nitriles, but separation of the byproduct phenol from the reaction is often tedious. The most recently reported methods in this category are presented here.
References
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