Relative Acidity and Basicity of Amines in THF and their influence on the Carbonylation of Lithium Amides

JORGE FURLONG; ELIZABETH LEWKOWICZ; NORMA SBARBATI NUDELMAN

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2

RSC

Lugar: Londres; Año: 1990 vol. 8 p. 1461 - 1465

0300-9580

The equilibrium constants for the ion-pair formation between 2,4-dinitrophenol and the following amines: pyrrolidine, piperidine, dibutylamine, di-isopropylamine, cyclohexylisopropylamine, dicyclohexylamine, morpholine, and diethylamine, in tetrahydrofuran (THF) have been measured. The relative acidities of the same amines (except diethylamine) have been also determined, as well as the pKa-values for di-isopropylamine, cyclohexylisopropylamine, and dicyclohexylamine in THF. The results show the importance of acid?base equilibria in determining the product distribution in the carbonylation of lithium amides in THF. They also explain the role of the [amine] : [amide] ratio in determining the reaction products