597-87-5Relevant academic research and scientific papers
Tf2O-Promoted Activating Strategy of Phosphate Analogues: Synthesis of Mixed Phosphates and Phosphinate
Huang, Hai,Ash, Jeffrey,Kang, Jun Yong
supporting information, p. 4938 - 4941 (2018/08/24)
A metal-, toxic chloride reagent-free activating strategy of various phosphates has been developed. This method enables the facile synthesis of functional phosphates such as alkyl phosphates, aza phosphates, thiophosphate, and mixed diaryl phosphates. A transient phosphorylpyridin-1-ium species in situ generated from phosphates with Tf2O/pyridine readily undergoes a substitution reaction with diverse nucleophiles to form versatile phosphate compounds.
Competing pathways in the photogeneration of didehydrotoluenes from (Trimethylsilylmethyl)aryl sulfonates and phosphates
Crespi, Stefano,Ravelli, Davide,Protti, Stefano,Albini, Angelo,Fagnoni, Maurizio
, p. 17572 - 17578 (2015/02/18)
The scope of the photochemical generation of a,n-didehydrotoluene diradicals from aryl sulfonates and phosphates and their chemistry are explored. The thermally inaccessible a,2- and a,4-intermediates are efficiently obtained by irradiation of ortho- and para-(trimethylsilylme-thyl)phenyl triflates through heterolytic splitting of the ester anion from the substrate in the triplet state. Triplet phenyl cations are formed and the loss of trimethylsilyl cation from them affords the desired diradicals (3Me3SiCH2C6H4-OZ→ 3Me3SiCH2C6H4+→CH2C6H4). Triplet sensitization is required, for which acetone is used throughout. Direct irradiation leads, on the contrary, to photo-Fries fragmentation (1Me3SiCH2C6H4O-Z→Me3SiCH2C6H4O· + Z). With mesylates, where ester cleavage is less convenient, a further competition from the triplet is direct desilylation. Didehydrotoluenes are also obtained from the corresponding phosphates, although with poor efficiency.
Triethylphosphate/phosphorus pentoxide as an efficient reagent for the phosphorylation of phenols
Kaboudin, Babak,Mostafalu, Ramin
experimental part, p. 776 - 780 (2012/06/30)
A simple, efficient, and novel method has been developed for the phosphorylation of phenols. Treatment of phenols with a mixture of triethylphosphate/phosphorus pentoxide gives the corresponding phosphate derivatives in good yields. This method is easy, rapid, and offers good yields for the phosphorylation of phenols. The reaction of triethylphosphate with phosphorus pentoxide was also studied by variable-temperature 31P-NMR spectroscopy. Copyright
