Photolysis of Phenacyl Esters in a Two-Phase System
| Authors | |
|---|---|
| Year of publication | 2002 |
| Type | Article in Periodical |
| Magazine / Source | Synthetic Communications |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | photoremovable protecting groups; photochemistry |
| Description | Phenacyl esters are useful photoremovable protecting groups for carboxylic acids in organic synthesis and biochemistry. In this work, simple one-pot arrangements of the phenacyl and 2,5-dimethylphenacyl ester photolysis are proposed. The reactions were performed in both the benzene/water two-phase system and in water. Cetyltrimethylamonium bromide was found to increase substantially the efficiency of the deprotection as well as the purity of the products by lowering the interfacial tension between the phases. Utilizing water as a medium significantly reduced the necessity to use environmentally malign organic solvents. The overall yields varied from 72 to 98 % depending on the reaction conditions. |
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