ORGN 493 |
| We report the cleaving of aryl alkyl ethers on BINOL derivatives, using the common reducing agent LiAlH4. The cleavage of the alkyl oxygen bond is observed when the BINOL derivative is treated with LiAlH4, in refluxing dioxane, for 60 hours. The resulting BINOL derivative can then be re-alkylated using a standard Williamson ether synthesis. The same procedure was tested on 6-hydroxy-2-naphthoic acid derivatives and cleavage was not observed, thus suggesting a chelating mechanism for the BINOL ether cleavage.
|
|
New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster
Division of Organic Chemistry |
