Simple Route to Adducts of (Amino)(aryl)carbene with Phosphorus Pentafluoride

Autor:	Alexander B. Rozhenko, Yuriy G. Shermolovich, Alexander N. Chernega, Yurii Vlasenko, Sergiy V. Zasukha, Olexandr I. Guzyr
Rok vydání:	2013
Předmět:	Reaction mechanism Aryl chemistry.chemical_element Ring (chemistry) Medicinal chemistry Adduct Inorganic Chemistry chemistry.chemical_compound Hydrolysis chemistry Fluorine Organic chemistry Phosphorus pentafluoride Carbene
Zdroj:	European Journal of Inorganic Chemistry. 2013:4154-4158
ISSN:	1099-0682 1434-1948
DOI:	10.1002/ejic.201300563
Popis:	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+.
Databáze:	OpenAIRE
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