Abstract Upon treatment with organolithium compounds, 2-alkyl-4, 5-dihydrofurans undergo ring opening through β-elimination leading to the corresponding 3, 4-dien-1-ol. If 3-chloro-2- methyl-4, 5-dihydrofuran serves as a substrate, however, no 3-chloro-3, 4-dien-1-ol can be isolated though it acts as a reaction intermediate. Its formation is slow compared to subsequent replacement of halogen by the organic moiety of the alkyllithium reagent. ...
