82026-89-9Relevant academic research and scientific papers
Metalated nitriles: Organolithium, -magnesium? and -copper exchange of α-halonitriles
Fleming, Fraser F.,Zhang, Zhiyu,Liu, Wang,Knochel, Paul
, p. 2200 - 2205 (2007/10/03)
(Chemical Equation Presented) α-Halonitriles react with alkyllithium, organomagnesium, and lithium dimethylcuprate reagents generating reactive, metalated nitriles. The rapid halogen-metal exchange with alkyllithium and Grignard reagents allows selective exchange in the presence of reactive carbonyl electrophiles, including aldehydes, providing a high-yielding alkylation protocol. Lithiated and magnesiated nitriles react with propargyl bromide by SN2 displacement whereas organocopper nitriles react by S N2′ displacement, correlating with the formation of a C-metalated nitrile.
Metalated Nitriles: Halogen - Metal Exchange with α-Halonitriles
Fleming, Fraser F.,Zhang, Zhiyu,Knochel, Paul
, p. 501 - 503 (2007/10/03)
(Equation presented) α-Halonitriles react with organometallic reagents in a facile halogen-metal exchange. The halogen-metal exchange is extremely fast with Grignard and alkyllithium reagents, generating metalated nitriles in situ with aldehyde, ketone, a
Influence of an α-Cyano Function on Charge Delocalization in the Benzyl Cation. Relationship between Inductive Destabilization and Conjugative Stabilization by the Cyano Group
Gassman, Paul G.,Guggenheim, Thomas L.
, p. 3023 - 3026 (2007/10/02)
The solvolytic behavior of a series of substituted acetophenone cyanohydrin methanesulfonates has been studied in 2,2,2-trifluoroethanol.A ρ value of -6.70 was observed when the rate data was evaluated vs.Brown's ?+ values.
