1459-16-1Relevant academic research and scientific papers
KrF excimer laser photolysis of 1,2-bis(substituted-methyl)benzenes in the presence of alkenes and acetylene; two-photon formation of o-quinodimethane and its cycloaddition with dienophiles
Ouchi, Akihiko,Koga, Yoshinori
, p. 2075 - 2076 (1996)
o-Quinodimethane 3 is generated effectively by KrF excimer laser (248 nm) photolysis of 1,2-bis(phenoxymethyl)-, 1,2-bis(phenylthiomethyl)- and 1,2-bis(phenylselenomethyl)-benzene via a two-photon process; cycloaddition of 3 with several dienophiles gives corresponding adducts in a maximum yield of 48%.
Electrochemical generation and reaction of o-quinodimethanes from {[[2-(2,2-dibutyl-2-stannahexyl)phenyl]-methyl]thio} benzenes
Jinno, Madoka,Kitano, Yoshikazu,Tada, Masahiro,Chiba, Kazuhiro
, p. 435 - 437 (2008/02/12)
(equation presented) The anodic oxidation of {[[2-(2,2-dibutyl-2-stannahexyl)phenyl]methyl]thio}benzenes gave o-quinodimethanes which were trapped in situ by dienophiles to give the corresponding cycloadducts in excellent yields. The electron transfer and succeeding 1,4-elimination reaction was efficiently completed in a solution of lithium perchlorate/nitromethane in the presence of acetic acid. The reaction progress was quantitatively controlled by the passage of charge. By using this new method, an aryltetralin lignan skeleton was also synthesized.
Electro-organic reactions. Part 41. Diels-Alder reaction of o-quinodimethanes from the cathodic reduction of α,α'-dibromo-1,2-dialkylbenzenes
Eru,Hawkes,Utley,Wyatt
, p. 3033 - 3044 (2007/10/02)
Cathodic reduction of α,α'-dibromo-1,2-dialkylbenzenes in DMF containing ET4N+ Br- as supporting electrolyte, in the presence of dienophiles (e.g. maleic anhydride derivatives), yielded Diels-Alder adducts of o-quinodimethanes. Selective reduction of the benzylic dibromides was often possible even when their irreversible cyclic voltammetric reduction peak potentials were more negative than the E(o) values for the anhydrides. This might be a consequence of redox catalysis, with the anhydrides having a dual role as mediators and dienophiles.
Metallic Nickel Assisted Room-Temperature Generation and Diels-Alder Chemistry of o-Xylylene Intermediates
Inaba, Shin-ichi,Wehmeyer, Richard M.,Forkner, Matthew W.,Rieke, Reuben D.
, p. 339 - 344 (2007/10/02)
Highly reactive metallic nickel, prepared by the lithium metal reduction of nickel iodide using naphthalene as an electron carrier, was found to induce 1,4-dehalogenation of α,α'-dihalo-o-xylene derivatives at room temperature.The reaction proceeds in the presence of a variety of electron-deficient olefins, giving Diels-Alder cycloadducts in moderate to good yields presumably via the highly reactive intermediate o-xylylene 2. 1,3-Dibromoindan and 1,4-dibromo-1,2,3,4-tetrahydronaphthalene also react in the presence of electron-deficient olefins to give bridged cycloadducts in moderate yields.Methoxy as well as electron-deficient substituents such as bromide and nitrile groups on the aromatic ring of the starting dibromide were shown to be compatible with the reaction conditions yielding substituted cycloadducts in good yields.
