(Z)-EtOCH:CHLi (I) reacts with carbonyl compds. as an acetaldehyde anion equiv. The exceptional stability of I is attributed mainly to an intramol. solvation mechanism. That the cis disposition of the Li and O atoms about the double bond, requisite of the intramol. solvation mechanism, is preferred even to halogen-metal exchange is illustrated in the formation of (E)-EtOCH:CBrLi from (E)-EtOCH:CHBr. [on SciFinder (R)]
Title
Selective syntheses with organometallics. 7. (Z)-2-Ethoxyvinyllithium: a remarkably stable and synthetically useful 1,2-counterpolarized species
Published in
Journal of Organic Chemistry
Volume
43
Issue
8
Pages
1595-8
Date
1978
Note
CAN 88:151816 22-8 Physical Organic Chemistry Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz. Journal 0022-3263 written in English. 65275-94-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 926-37-4P; 5623-82-5P; 14371-10-9P; 54277-04-2P; 65275-93-6P; 65275-95-8P; 65275-96-9P; 65275-97-0P; 65392-07-6P; 154354-36-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 16339-88-1; 23521-49-5 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with butyllithium); 100-39-0 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with ethoxyphenylpropenol and sodium hydride); 75-97-8; 100-52-7; 120-92-3; 630-19-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with ethoxyvinyllithium); 64724-28-3 Role: PRP (Properties) (reactivity of, intramol. solvation in relation to)
Record creation date
2006-03-03
