77008-59-4Relevant articles and documents
Palladium-catalyzed synthesis of diarylmethanes: Exploitation of carbanionic leaving groups
Schmink, Jason R.,Leadbeater, Nicholas E.
, p. 2575 - 2578 (2009)
A novel route to the synthesis of diarylmethanes via a Pd-catalyzed α-arylation of benzyl ketones is rseported. By harnessing the inherent reactivity of enolates, it is possible to circumvent the need for a transmetalating reagent such as boron for the co
Kinetics of the solvolyses of benzhydryl derivatives: Basis for the construction of a comprehensive nucleofugality scale
Denegri, Bernard,Streiter, Andre,Juric, Sandra,Ofial, Armin R.,Kronja, Olga,Mayr, Herbert
, p. 1648 - 1656 (2007/10/03)
A series of 21 benzhydrylium ions (diarylmethylium ions) are proposed as reference electrofuges for the development of a general nucleofugality scale, where nucleofugality refers to a combination of leaving group and solvent. A total of 167 solvolysis rate constants of benzhydrylium tosylates, bromides, chlorides, trifluoroacetates, 3,5-dinitrobenzoates, and 4-nitroben-zoates, two-thirds of which have been determined during this work, were subjected to a least-squares fit according to the correlation equation log k 25°C = Sf(Nf + Ef), where s f and Nf are nucleofuge-specific parameters and E f is an electrofuge-specific parameter. Although nucleofuges and electrofuges characterized in this way cover more than 12 orders of magnitude, a single set of the parameters, namely sf, Nf, and E f, is sufficient to calculate the solvolysis rate constants at 25°C with an accuracy of ± 16%. Because sf ≈ 1 for all nucleofuges, that is, leaving group/ solvent combinations, studied so far, qualitative discussions of nucleofugality can be based on Nf.
