166190-04-1Relevant academic research and scientific papers
Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents
Habermann, Joerg,Ley, Steven V.,Smits, Rene
, p. 2421 - 2423 (2007/10/03)
An efficient combinatorial route to substituted 3-phenyl-benzofurans, is achieved by the bromination of acetophenones to α-bromoacetophenones by polymer-supported pyridinium bromide perbromide (PSPBP). The subsequent clean substitution of the obtained bromides by phenols using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD-P) and cyclodehydration of the resulting α-phenoxyacetophenones using Amberlyst 15, affords pure products without the need for any chromatographic purification step.
Photochemical Generation of Radical Anions of Photolabile Aryl Ketones
Mathivanan, N.,Johnston, L. J.,Wayner, D.D.M.
, p. 8190 - 8195 (2007/10/02)
The radical anions of a series of substituted α-(aryloxy)acetophenones have been generated by trapping the solvated electron produced by 355-nm laser-induced photoionization of 4,4'-dimethoxystilbene in either acetonitrile or dimethylformamide (DMF).The radical anion of the parent ketone, α-phenoxyacetophenone, has λmax at 500 nm and decays with a rate constant 7 x 1E5 s-1.This rate constant reflects the rate of β-cleavage to generate phenoxide ion and phenylacyl radical.The rate constant for β-cleavage decreases for ketones with electron donating substituents in the α-aryloxy ring.Substituent effects on the acetophenone ring are in the opposite direction, and many of the 4-substituted (aryloxy)acetophenones have half-lives in excess of 10 μs that reflect a combination of second order processes and are not limited by β-cleavage.The generality of the photoionization/electron trapping method for the generation of radical anions of ketones with short-lived excited states that preclude direct excitation is illustrated by its application to other aryl ketones that undergo α-cleavage, β-phenyl quenching, and intramolecular hydrogen abstraction reactions.
