Formation of 3-Halobenzyne: Solvent Effects and Cycloaddition Adducts
Noncoordinating solvents permit the halogen−metal exchange-induced formation of benzyne (aryne) from di- and trihalobenzene precursors in the presence of cyclopentadiene to give 1,4-dihydro-1,4-methano-naphthalenes. Studies with mixed halide precursors and nonacidic Diels−Alder diene traps reveal th...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2004-05, Vol.6 (10), p.1589-1592 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| Zusammenfassung: | Noncoordinating solvents permit the halogen−metal exchange-induced formation of benzyne (aryne) from di- and trihalobenzene precursors in the presence of cyclopentadiene to give 1,4-dihydro-1,4-methano-naphthalenes. Studies with mixed halide precursors and nonacidic Diels−Alder diene traps reveal that ethereal and hydrocarbon solvents influence the halide leaving group facility, resulting in a reversal of 3-halobenzyne regioselectivity. |
|---|---|
| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/ol049655l |