Crowley, Patrick J and Fawcett, John and Kariuki, Benson M and Moralee, Andrew C and Percy, Jonathan and Salafia, Vittoria (2002) Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes. Organic Letters, 4 (23). pp. 4125-4128. ISSN 1523-7060
Full text not available in this repository. (Request a copy from the Strathclyde author)Abstract
Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC ) CONEt2) to afford lactone 8, which can be reduced and protected in a series of high-yielding steps. Key sulfone 10 can be ring opened under strong base conditions to afford vinyl sulfone 11. Attempted desulfonation resulted in the formation of a monofluoroalkene, but a direct desulfonation/eliminative ring opening with strain relief delivered highly functionalized monocyclic species 16.
| Item type: | Article |
|---|---|
| ID code: | 38951 |
| Keywords: | strain relief, monofluoroalkene, ring opening, Chemistry |
| Subjects: | Science > Chemistry |
| Department: | Faculty of Science > Pure and Applied Chemistry |
| Related URLs: | |
| Depositing user: | Pure Administrator |
| Date Deposited: | 04 Apr 2012 14:50 |
| Last modified: | 04 Apr 2012 14:50 |
| URI: | http://strathprints.strath.ac.uk/id/eprint/38951 |
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