41245-70-9Relevant articles and documents
Quinone C-H Alkylations via Oxidative Radical Processes
Hamsath, Akil,Galloway, Jordan D.,Baxter, Ryan D.
supporting information, 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.
Total synthesis of parvaquone and the serendipitous discovery of a novel chromium-mediated method for β-lactone formation
Harrity, Joseph P. A.,Kerr, William J.,Middlemiss, David,Scott, James S.
, p. 219 - 227 (2007/10/03)
During attempts to synthesise the 2-hydroxy-1,4-naphthoquinone, parvaquone, 1, a novel chromium-mediated method for the synthesis of functionalised β-lactones from propargyl alcohols has been discovered. Additionally, using both dry state and ultrasound conditions, the total synthesis of parvaquone (1) has been achieved; the most efficient techniques deliver this target compound in up to 46% overall yield over, as low as, two synthetic processes.
