Abstract
A series of adducts of LiCN, namely [Li(Me2CO3)CN], [Li(Et2CO3)CN], and [Li(NMP)CN] (NMP = N-methyl-2-pyrrolidone) were prepared by treatment of solvent-free LiCN with the appropriate donor. The starting material for these approaches, donor-free LiCN, was quantitatively prepared from Me3SiCN and Li[Me] in diethyl ether at 0 °C. Alternatively, [Li(NMP)CN] was synthesized by metathesis reaction of LiCl with NaCN in the presence of stoichiometric amounts of NMP. Although [Li(Me2CO3)CN] and [Li(Et2CO3)CN] are water-sensitive compounds and decompose at the exposure to air, [Li(NMP)CN] is stable in air, even at elevated temperatures. The thermal stability of [Li(NMP)CN] was proven by differential thermal analysis (DTA). [Li(NMP)CN] shows thermal stability up to temperatures of about 132 °C. To evaluate the cyanation ability the reactions of 1-bromooctane and 3-bromocyclohexene with unsupported LiCN, [Li(NMP)CN], and a mixture of NaCN/LiCl/NMP were investigated. We found that [Li(NMP)CN] as well as LiCl/NaCN/NMP are efficient cyanation reagents comparable to the expensive and air-sensitive, donor-free LiCN. A product of the chloride-cyanide-bromide exchange could be isolated and structurally characterized by X-ray diffraction.
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