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)]


Published in:
Helvetica Chimica Acta, 58, 2, 556-64
Year:
1975
Keywords:
Note:
CAN 83:9072
23-7
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0018-019X
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)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)