title: Highly selective 1,4- and 1,6-addition of P(O)-H compounds to p-quinones: a divergent method for the synthesis of C- and O-phosphoryl hydroquinone derivatives.
abstract: The reaction of P(O)-H compounds with p-quinones could proceed through either 1,4- or 1,6-addition pathways by employing different additives to selectively give the corresponding C- and O-phosphoryl hydroquinone derivatives in good yields. Oxidative double 1,4-addition of P(O)-H compounds to p-quinones was also achieved by tuning the solvent, affording a facile synthesis of bis-substituted hydroquinones with phosphorus functionality. Further studies on these reactions by using optically active H-phosphinates showed that all addition reactions took place stereospecifically with retention of configuration at the phosphorus center. The findings lead to the establishment of a divergent method for the synthesis of C- and O-phosphoryl hydroquinone derivatives from easily available P(O)-H compounds.
authors.affiliation: Department of Chemistry, College of Chemistry and Chemical Engineering, Hunan University, Changsha, PR China.
authors.forename: Biquan
authors.initials: B
authors.lastname: Xiong
authors.forename: Ruwei
authors.initials: R
authors.lastname: Shen
authors.forename: Midori
authors.initials: M
authors.lastname: Goto
authors.forename: Shuang-Feng
authors.initials: SF
authors.lastname: Yin
authors.forename: Li-Biao
authors.initials: LB
authors.lastname: Han
mesh_terms: D006859:Hydrogen / Q000737:chemistry; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010721:Phosphinic Acids / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006873:Hydroquinones; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D010721:Phosphinic Acids; D011809:Quinones; D006859:Hydrogen