title: Intramolecular arene epoxidation by phosphadioxiranes.
abstract: Singlet oxygen reacts with binaphthyl phosphine derivatives such as 1,1'-binaphthyl di-tert-butyl phosphine to form the corresponding binaphthyl-2-oxide phosphine oxides. This new intramolecular arene epoxidation reaction proceeds with complete retention of stereochemistry. The binaphthyl-2-oxide di-tert-butyl phosphine oxide undergoes a slow "NIH-rearrangement" to form the corresponding hydroxylated product. A transient phosphadioxirane intermediate has been directly observed by low-temperature NMR. Kinetic analyses show that all of the phosphadioxirane intermediate is converted to product. [reaction: see text]
authors.affiliation: Department of Chemistry and Biochemistry, California State University-Los Angeles, Los Angeles, CA 90032, USA.
authors.forename: Dong
authors.initials: D
authors.lastname: Zhang
authors.forename: Ruomei
authors.initials: R
authors.lastname: Gao
authors.forename: Shabana
authors.initials: S
authors.lastname: Afzal
authors.forename: Mario
authors.initials: M
authors.lastname: Vargas
authors.forename: Shantanu
authors.initials: S
authors.lastname: Sharma
authors.forename: Alison
authors.initials: A
authors.lastname: McCurdy
authors.forename: Muhammed
authors.initials: M
authors.lastname: Yousufuddin
authors.forename: Timothy
authors.initials: T
authors.lastname: Stewart
authors.forename: Robert
authors.initials: R
authors.lastname: Bau
authors.forename: Matthias
authors.initials: M
authors.lastname: Selke
mesh_terms: D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D009281:Naphthalenes; D010720:Phosphines; D010100:Oxygen