2,2-Diethoxyvinyllithium (I) can be readily generated from 2-bromo-1,1-diethoxyethylene by treatment with butyllithium. Reaction of I with electrophiles e.g. chlorotrimethylsilane gives Me3SiCH:C(OEt)2. When dissolved in THF, I can be stored at -25 DegC for hours, but decomps. rapidly at 0 DegC. [on SciFinder (R)]
Titre
2,2-Di(ethoxy)vinyllithium: a synthetic equivalent of the ethyl acetate anion
Publié dans
Tetrahedron Letters
Volume
37
Numéro
16
Pages
2771-2772
Date
1996
ISSN
0040-4039
Note
CAN 125:33140
23-17
Aliphatic Compounds
Inst. Chimie Organique de l'Universite,Batiment de Chimie (BCh),Lausanne-Dorigny,Switz.
Journal
written in English.
177544-54-6 Role: FMU (Formation, unclassified), RCT (Reactant), FORM (Formation, nonpreparative), RACT (Reactant or reagent) (di(ethoxy)vinyllithium as synthetic equiv. of Et acetate anion); 75-77-4 (Chlorotrimethylsilane); 77-78-1 (Dimethyl sulfate); 100-39-0 (Benzyl bromide); 100-52-7 (Benzaldehyde); 104-88-1 (p-Chlorobenzaldehyde); 123-72-8 (Butanal); 630-19-3 (Pivalaldehyde); 4360-66-1; 7553-56-2 (Iodine); 7790-99-0 (Iodonium chloride); 42520-11-6; 98921-98-3 Role: RCT (Reactant), RACT (Reactant or reagent) (di(ethoxy)vinyllithium as synthetic equiv. of Et acetate anion); 103-36-6P; 6048-06-2P; 21504-43-8P; 63473-79-0P; 87995-20-8P; 96694-11-0P; 96694-12-1P; 177544-52-4P; 177544-53-5P; 177544-55-7P Role: SPN (Synthetic preparation), PREP (Preparation) (di(ethoxy)vinyllithium as synthetic equiv. of Et acetate anion)
Date de création de la notice
2006-03-03
