ORGN 503 |
| As part of a broad investigation of the chemistry of sulfinylindoles, we have become interested in the potential of N-sulfinyl groups to serve as handles for introducing functionality at indole C7 or C3. N-sulfinylindoles were conveniently prepared via mCPBA oxidation of the corresponding N-sulfenylindoles. While neat samples of the N-sulfinyindoles decomposed to parent indoles at low temperature, the sulfinylindoles proved to be stable for days at rt as 0.3 M solutions in non-nucleophilic solvents. We have observed the cerium(III)chloride promoted rearrangement of N-(methylsulfinyl)indole to the corresponding 3-methanesulfenate, and observation of that N- to C3 rearrangement has led to the development of strategies for directing analogous chemistry from N- to C7. Preparative methods, mechanistic considerations, and plans for future studies of N-sulfinylindoles will be presented.
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Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |
