77312-81-3Relevant academic research and scientific papers
Synthesis and Photochemical Isomerization of 1,2-Di-9-anthrylethanol and 1,2-Di-9-anthrylethanone
Becker, Hans-Dieter,Hansen, Lars,Andersson, Kjell
, p. 2956 - 2961 (2007/10/02)
1,2-Di-9-anthrylethanol has been synthesized by Grignard reaction of 9-anthrylmagnesium bromide with 9-anthrylacetaldyhyde which, in turn, was obtained by oxidation of 9-anthrylethanol with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one ("Dess-Martin periodinane").This oxidant also was found to be the reagent of choice for the conversion of dianthrylethanol into 1,2-di-9-anthrylethanone.The photochemical isomerization of dianthrylethanol in benzene solution proceeds with a quantum yield of 0.34 by intramolecular cycloaddition involving the excited singlet state.Remarkably, the course of photochemical isomerization of 1,2-di-9-anthrylethanone is dependent on the substrate concentration, affording mainly intramolecular cyclomers in dilute (0.00001 M) solution but the intramolecular cycloadduct in concentrated (0.01 M) solution.The proposed triplet state pathway for the formation of intramolecular Diels-Alder products from dianthrylethanone is supported by oxygen quenching results and sensitization experiments with biacetyl.The photochemical isomerization of di-9-anthryl ketone and 1,3-di-9-anthrylpropan-1-one gives rise to intramolecular (ψ=0.0003) and (ψ=0.65) cycloadducts, respectively.The differences in quantum yields and modes of cycloaddition are attributed to differences in molecular geometry.
Reaktionen mit Radikalanionen, IV. Synthese von Mono- und Diketonen aus Carboxyl- und α,β-ungesaettigten Carbonyl-Verbindungen
Kirrstetter, Reiner G. H.,Vagt, Uwe
, p. 630 - 637 (2007/10/02)
1,2-Diketones of the benzil type were obtained in the reaction of aromatic carboxylic compounds with lithium naphthalenide.The scope of this reaction was investigated. α,β-Unsaturated ketones yielded hydrodimerisation, hydrogenation and hydroxylation products.
