One Step Synthesis of Calix[n]quin­ones through the HClO4/PbO2‐Mediated Oxidation of Calix[n]arenes. Issue 9 (4th March 2016)

• Record Type: Journal Article
• Authors: Lavendomme, Roy; Troian‐Gautier, Ludovic; Zahim, Sara; Reinaud, Olivia; Jabin, Ivan
• Is Part Of: European journal of organic chemistry. Issue 9(2016)
• Page Start: 1665
• Page End: 1668
• Publication Date: 2016-03-04
• Subjects: Calixarenes -- Quinones -- Oxidation -- Synthetic methods -- Macrocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600092
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A procedure using HClO4 and PbO2 allows the straightforward oxidation of para ‐substituted and unsubstituted calix[ n ]arenes into the corresponding calix[ n ]quinones in approximately 82 % yield per quinone unit. These mild conditions constitute a good alternative to the classical procedure that involves highly toxic thallium(III) salts in trifluoroacetic acid. Abstract : Direct oxidation of para ‐substituted and unsubstituted calix[ n ]arenes into the corresponding calix[ n ]quinones was achieved with HClO4 and PbO2 in approximately 82 % yield per quinone unit. This method constitutes an efficient alternative to the classical procedure that involves highly toxic thallium(III) salts.