102001-55-8Relevant academic research and scientific papers
Quinone C-H Alkylations via Oxidative Radical Processes
Hamsath, Akil,Galloway, Jordan D.,Baxter, Ryan D.
, p. 2915 - 2923 (2018/06/12)
A brief survey of radical additions to quinones is reported. Carboxylic acids, aldehydes, and unprotected amino acids are compared as alkyl radical precursors for the mono- or bis- C-H alkylation of several quinones. Two methods for radical initiation are discussed comparing inorganic persulfates and Selectfluor as stoichiometric oxidants. Kinetic analysis reveals dramatic differences in the rate of radical initiation depending on the identity of the radical precursor and oxidant. Synthetic strategies for efficiently producing alkyl-quinones are discussed in the context of selecting optimum radical precursors and initiators depending on quinone identity and functional groups present.
The reaction of nitrile oxide-quinone cycloadducts. III. Reinvestigation of the base-induced isomerization of the 1:1 -C=C-adducts of aromatic nitrile oxides with 2,5-and 2,6-dialkyl-substituted p-benzoquinones
Mukawa, Takashi,Inoue, Yukihiko,Shiraishi, Shinsaku
, p. 2549 - 2556 (2007/10/03)
The structure of the product obtained by the base, induced isomerization of the 1,3-dipolar cycloadduct of 2,5-di-t-butyl-p-benzoquinone with 2,6- dichlorobenzonitrile oxide was determined by X-ray analysis. The t-butyl group at the bridgehead position of the 1,3-dipolar cycloadduct migrated to the neighboring carbonyl carbon atom. This base-induced rearrangement took place with a bulky group, i.e., Et, i-Pr, t-Bu, and Bn at the bridgehead position of nitrile oxide-quinone cycloadducts in an alcoholic media. The driving force of this reaction is considered to be due to stabilization by aromatization from isoxazoline derivatives to isoxazole-fused p-quinol derivatives.
