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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Bibliographic Details
Published in:Organic letters 2004-05, Vol.6 (10), p.1589-1592
Main Authors: Coe, Jotham W, Wirtz, Michael C, Bashore, Crystal G, Candler, John
Format: Article
Language:English
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Summary: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