title: Selective oxidation of 8,8'-hydroxylated binaphthols to bis-spironaphthalenones or binaphtho-para- and binaphtho-ortho-quinones.
abstract: The selective oxidation of a series of functionalized 8,8'-hydroxylated binaphthols to binaphtho-para- and binaphtho-ortho-quinones has been realized using either a Co-salen catalyst or ortho-iodoxybenzoic acid. A unique spirocyclic bis-spironaphthalenone was also obtained in good yield via a phenyliodonium diacetate promoted oxidative dearomatization.
authors.affiliation: Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
authors.forename: Erin E
authors.initials: EE
authors.lastname: Podlesny
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll
authors.forename: Marisa C
authors.initials: MC
authors.lastname: Kozlowski
mesh_terms: D002384:Catalysis; D005029:Ethylenediamines / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005029:Ethylenediamines; D009284:Naphthols; D011809:Quinones; D013141:Spiro Compounds; C011452:disalicylaldehyde ethylenediamine