Elimination of 3-Hydroxy-2-nitro-2, 3-dihydrobenzo[b]furans to 2-Nitrobenzo[b]furans
キーワード:
isotope effect
1988 年 36 巻 4 号 p. 1336-1342
詳細
1988 年 36 巻 4 号 p. 1336-1342
β-Elimination of stereoisomeric cis- and trans-3-hydroxy-2-nitro-2, 3-dihydrobenzo[b]furans was investigated. The 2, 3-dihydrobenso[b]furans were stable under acidic conditions but were easily dehydrated under basic conditions to afford the corresponding 2-nitrobenzo[b]furans. An (ElcB)R mechanism is proposed on the basis of several lines of evidence obtained from studies on kinetics, ultraviolet spectra, leaving group effect and deuterium isotope effect in the elimination reaction.
