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)]
Title
Hydroxyäthylallene und andere Folgeprodukte aus Dihydrofuran-Derivaten
Published in
Helvetica Chimica Acta
Volume
58
Issue
2
Pages
556-64
Date
1975
ISSN
0018-019X
Note
CAN 83:9072
23-7
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
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 creation date
2006-03-03
