Anti and syn eliminations from 2, 3-dihalo-2, 3-dihydrobenzofurans. The role of the substrate structure and the base-solvent system on the reaction mechanism

…, R Ruzziconi, GV Sebastiani

Index: Baciocchi, Enrico; Ruzziconi, Renzo; Sebastiani, Giovanni V. Journal of the American Chemical Society, 1983 , vol. 105, # 19 p. 6114 - 6120

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Citation Number: 16

Abstract

Abstract: The anti and syn@-eliminations from a series of 3 1 2, 3-dihalo-2, 3- dihydrobenzofurans (to give 3-halobenzofuran) have been kinetically investigated in t-BuOK- t-BuOH, in the presence and in the absence of 18-crown-6 ether (1 8C6), and in EtOK-EtOH. Reaction mechanisms have been assigned on the basis of leaving group, kinetic deuterium isotope, ring substituent (5-chlorine), and@-halogen effects. These data have provided ...