Syntheses and reactivity of naphthalenyl-substituted arenediynes.
| Autor: | Korovina NV; Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, California 95819, USA., Chang ML, Nguyen TT, Fernandez R, Walker HJ, Olmstead MM, Gherman BF, Spence JD |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2011 Jul 15; Vol. 13 (14), pp. 3660-3. Date of Electronic Publication: 2011 Jun 13. |
| DOI: | 10.1021/ol201317w |
| Abstrakt: | A series of naphthalenyl-substituted arenediynes were prepared to examine photochemical reactivity. For naphthalen-1-ylethynyl arenediyne, 350 nm photolysis resulted in a tandem [2 + 2] photocycloaddition to afford cyclobutene adducts. For naphthalen-2-ylethynyl derivatives, electron-donating methoxy substituents were found to facilitate C(1)-C(6) Bergman cyclization at 300 nm. Theoretical calculations provided further insight into thermal and photochemical reactivity. (© 2011 American Chemical Society) |
| Databáze: | MEDLINE |
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