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19.5.4 Introduction of the Cyano Group by Substitution of Metals

DOI: 10.1055/sos-SD-019-00121

Subramanian, L. R.Science of Synthesis, (200419163.

General Introduction

Organometallic compounds are very reactive species which find widespread use as reagents in CC 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.

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