199-94-0Relevant articles and documents
Thermal reduction of 7H-benz[d,e]anthracen-7-one and related ketones under hydrogen-transfer conditions
Mulder,Hemmink,De Heer,Lupo,Santoro,Korth
, p. 6611 - 6619 (2007/10/03)
In the presence of hydrogen donor solvents and at elevated temperatures, aromatic ketones can be selectively deoxygenated to the corresponding hydroaromatic compounds. The kinetics for reduction of 7H-benz[d,e]anthracen-7-one (benzanthrone, 6) into 7H-benz[d,e]anthracene (benzanthrene, 1) in 9,10-dihydroanthracene (3) solvent has been investigated in detail. The relatively slow hydrogenation of 6 is due to reversibility of the initial hydrogen-transfer step according to a reverse radical disproportionation (RRD). The dynamics could well be rationalized using the energetics of species computed by density functional theory (DFT). The application of hydrogen donors such as 1 as a hydrogen-transfer agent, although favorable in terms of a low benzylic carbon-hydrogen bond dissociation enthalpy, is limited due to the slow self-hydrogenation, which in case of 1 gives 5,6-dihydro-4H-benz[d,e]anthracene (7).
Equilibrium acidities of some sulfones and sulfoxides in tetrahydrofuran
Streitwieser, Andrew,Wang, George Peng,Bors, Daniel A.
, p. 10103 - 10112 (2007/10/03)
Ion pair acidities are reported in tetrahydrofuran (THF) solution for the lithium and cesium salts of several sulfones and one sulfoxide. These salts are shown to be monomeric in the THF solutions studied. Thermodynamic constants are reported for several salts. The results and some conductivity studies show that both the lithium and cesium salts are contact ion pairs in THF. Because of ion association the relative pKs are slightly lower for cesium salts and much lower for lithium salts than for the free ions in DMSO solution.