O. Guzyr, S. Zasukha, Y. Vlasenko
Aug 12, 2013
Citations
1
Influential Citations
8
Citations
Journal
European Journal of Inorganic Chemistry
Abstract
The tetramethyl ester of (hydroxy)(phenyl)methylenebis(phosphonic acid) reacts with morpholinosulfur trifluoride (MOST) to provide, along with the expected product of the substitution of a hydroxy group by fluorine, the adduct of (morpholino)(phenyl)carbene with PF5, compound 3a. Fluorination of dimethyl α-aroylphosphonates with MOST yields adducts of (amino)(aryl)carbene with PF5 (p-XC6H4)(Morph)C:PF5 [3a–f, where Morph is morpholyl, X = H (a), Me (b), OEt (c), F (d), Cl (e), CF3 (f)] as the major reaction products. The reaction mechanism proposed is based on experimental data and DFT calculations. The structure of adduct 3a was determined by X-ray studies. Hydrolysis of compounds 3e and 3f, bearing substituents Cl and CF3 on the phenyl ring, respectively, yields previously unknown benzoylpentafluorophosphates [p-XC6H4–C(=O)PF5]–MorphH+.