2,5-dimethylphenacyl esters: a photoremovable protecting group for phosphates and sulfonic acids.
2,5-Dimethylphenacyl phosphoric and sulfonic esters release the corresponding acids upon irradiation in nearly quantitative isolated yields, with quantum yields phi = 0.71 and 0.68 in methanol, 0.09 and 0.19 in benzene. In methanol solution the reactions proceed predominantly via the (Z)-photoenol, the lifetimes of which (20 and 25 micros) were determined by laser flash photolysis. The chromophore is proposed as an excellent photoremovable protecting group for use in organic synthesis and biochemistry.
Klán
Petr
P
Department of Organic Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, CZ-611 37 Brno, Czech Republic. klan@sci.muni.cz
Pelliccioli
Anna Paola
AP
Pospísil
Tomás
T
Wirz
Jakob
J
D000098:Acetophenones / Q000737:chemistry; D001554:Benzene / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D007536:Isomerism; D007700:Kinetics; D007834:Lasers; D000432:Methanol / Q000737:chemistry; D010755:Organophosphates / Q000737:chemistry*; D010777:Photochemistry / Q000379:methods; D010782:Photolysis; D011789:Quantum Theory; D013451:Sulfonic Acids / Q000737:chemistry*
D000098:Acetophenones; D004952:Esters; D010755:Organophosphates; D013451:Sulfonic Acids; D001554:Benzene; D000432:Methanol