Hydroxyäthylallene und andere Folgeprodukte aus Dihydrofuran-Derivaten
Upon treatment with organolithium compds., 2-alkyl-4,5-dihydrofurans underwent ring opening through b-elimination to give the corresponding 3,4-dien-1-ol. 3-Chloro-2-methyl-4,5-dihydrofuran gave 3-chloro-3,4-dien-1-ol as a reaction intermediate, but it could not be isolated. Its formation was slow compared to subsequent replacement of halogen by the org. moiety of the alkyllithium reagent. Under certain reaction conditions, the 3,4-pentadien-1-ol which formed isomerized to terminal acetylenes, which, as well as their allene precursors, could be converted with Na-NH3 into 4-penten-1-ol or 3-penten-1-ol derivs. [on SciFinder (R)]
Keywords: Alcohols Role: PREP (Preparation) (allenic ; by ring cleavage of dihydrofurans by organolithiums); Ring cleavage (of dihydrofurans in reaction with organolithiums) ; organolithium furan ring cleavage; alkyldienol; alkyne; ene ether reaction organlithium
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
written in German.
5390-04-5P; 10229-10-4P; 18022-52-1P; 54795-23-2P; 55930-35-3P; 55930-36-4P; 55930-37-5P; 55930-38-6P; 55930-39-7P; 55930-40-0P; 55930-41-1P; 55930-42-2P; 55930-43-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 4111-54-0 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with chlorodihydromethylfuran); 594-19-4; 917-54-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with dihydrofurans); 50596-94-6 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with organolithiums); 50596-99-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with tert-Bu lithium); 109-72-8 Role: RCT (Reactant), RACT (Reactant or reagent) (with dihydrofurans)
Record created on 2006-03-03, modified on 2016-08-08