Formation of 3-Halobenzyne: Solvent Effects and Cycloaddition Adducts
Organic Letters2004Vol. 6(10), pp. 1589–1592
Citations Over TimeTop 18% of 2004 papers
Abstract
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.
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