The Power of Solvent in Altering the Course of Photorearrangements
Název česky | Schopnost rozpouštědla měnit mechanismus fotochemického přesmyku |
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Autoři | |
Rok publikování | 2011 |
Druh | Článek v odborném periodiku |
Časopis / Zdroj | Organic Letters |
Fakulta / Pracoviště MU | |
Citace | |
Doi | http://dx.doi.org/10.1021/ol102887f |
Obor | Organická chemie |
Klíčová slova | Photochemistry; photo-Favorskii rearrangement; water |
Popis | A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzofuranones occurs abruptly at low water concentrations (~8%). The surprisingly clean yields suggest that such reactions are synthetically promising. |
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