Abstract
A stoichiometric cobalt-promoted acrylonitrile (AN) coupling reaction leading to adiponitrile (ADN) formation was reinvestigated. The active catalyst appears to involve cobalt(0) species. Cobalt hydride complexes are either inactive [CoH 2(PPh 3) 3] or give only low yields of ADN [CoH(N 2)(PPh 3) 3]. Intermediate Co(AN) 2 species can be reduced to give ADN using H 2S or using H 2 and Pt on C. Choice of ligand is a factor in determination of ADN yield, such yields decreasing in the order (CH 3) 2NCHO ≅ PPh 3>P(OPh) 3>P(CH 3) 3>P(OC 2H 5) 3. Formation of stoichiometric ADN yields from Co(N 2)(PPh 3) 3 and AN indicate that co-promoters, such as ZnCl 2 and CoCl 2, are not required. Different ADN/ c,t-1,4-dicyanobutene-1 product ratios, obtained by H 2S treatment of Co(AN) 2 species and a known ▪ complex, suggest that the intermediate Co(AN) 2 species consist mainly of polymeric structures rather than monomeric metallacyclic complexes.
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