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...
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Veröffentlicht in: | Organic letters 2004-05, Vol.6 (10), p.1589-1592 |
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creator | Coe, Jotham W Wirtz, Michael C Bashore, Crystal G Candler, John |
description | 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. |
doi_str_mv | 10.1021/ol049655l |
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title | Formation of 3-Halobenzyne: Solvent Effects and Cycloaddition Adducts |
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