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19.5.4.2 Method 2: From Organocopper Compounds

DOI: 10.1055/sos-SD-019-00121

Subramanian, L. R.Science of Synthesis, (200419165.

Although no systematic studies have been carried out, organocopper compounds have found sporadic use as intermediates in obtaining the corresponding nitrile as described for the preparation of phenylacetonitrile (6) from benzylzinc bromide (4)[‌11‌] (see Scheme 2, Section 19.5.4.1). One example of the direct conversion of an organocopper compound into its nitrile derivative is the formation of (2E)-3-phenylacrylonitrile (8) with retention of configuration via the cyanation of organocopper compound 7 with 2-pyridyl cyanate (see Section 19.5.4.3). Organocopper compound 7 is generated by the transmetalation of trimethyl[(E)-2-phenylvinyl]stannane with dilithium cyanodimethylcuprate (Scheme 3).[‌14‌]

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