10384-20-0Relevant academic research and scientific papers
Regio- and diastereoselective reduction of nonenolizable α-diketones to acyloins mediated by indium metal
Khan, Faiz Ahmed,Dash, Jyotirmayee,Sahu, Nilam,Gupta, Sharad
, p. 1015 - 1018 (2007/10/03)
(equation presented) α-Diketones are efficiently reduced with indium metal in methanol-water in the presence of NH4Cl, LiCl, or NaCl to give regio-and diastereoselectively the corresponding acyloins in good to excellent yield. The cleavage of the acyloins under Pb(OAc)4MeOH-PhH condition provides a convenient and regioselective access to highly functionalized cyclopentane carboxaldehydes, potential building blocks in organic syntheses.
Minor Products in Photoreactions of α-Diketones with Arenes. Abstraction of Hydroxylic Hydrogen by Triplet Carbonyl
Rubin, Mordecai B.,Gutman, Arie L.
, p. 2511 - 2515 (2007/10/02)
Photochemical reactions of cyclic saturated α-diketones in toluene or p-xylene produce 1:1 adducts as major products and smaller amounts of reduced diketone and bibenzyls, as expected from previous work.In addition, reaction of BOD gave 2percent of the decarbonylation product, p-methylbenzyl cyclohexyl ketone; reaction of camphorquinone gave a mixture of decarbonylation products (10percent total) including saturated and unsaturated monoketones.These compounds were secondary products arising from reaction of photoexcited diketone with the initially formed adducts; quenching andsensitization studies showed that triplet states of α-diketones were involved in both primary and secondary reactions.The decarbonylation products were also formed by reaction of benzophenone triplets or of tert-butoxy radicals with adducts.Deuterium labeling of the adducts was employed to demonstrate that the decarbonylation process involves abstraction of hydroxylic hydrogen.
