The Power of Solvent in Altering the Course of Photorearrangements
| Authors | |
|---|---|
| Year of publication | 2011 |
| Type | Article in Periodical |
| Magazine / Source | Organic Letters |
| MU Faculty or unit | |
| Citation | |
| Doi | http://dx.doi.org/10.1021/ol102887f |
| Field | Organic chemistry |
| Keywords | Photochemistry; photo-Favorskii rearrangement; water |
| Description | 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. |
| Related projects: |