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Selective syntheses with organometallics. 7. (Z)-2-Ethoxyvinyllithium: a remarkably stable and synthetically useful 1,2-counterpolarized species

(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)]

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