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8428366 
Journal Article 
Pure, Unsolvated (α-Methoxyvinyl)lithium and Related Acyl Anion Equivalents via the Transmetalation of Organotin Compounds 
Soderquist, JA; Hsu, GJH 
1982 
1 
Organometallics
ISSN: 0276-7333
EISSN: 1520-6041 
1 
6 
830-833 
English 
A detailed study of the deprotonation of simple vinyl ethers is reported. The major α-deprotonation reaction is accompanied by a temperature-dependent β-deprotonation process. Pure, unsolvated (α-methoxyvinyl)lithium and related acyl anion equivalents can be prepared quantitatively from the transmetalation of (α-methoxyvinyl)tin compounds using n-butyllithium in hexane solution. These lithiated compounds are useful intermediates for the preparation of α-deuterated and silylated vinyl ethers, the latter providing an efficient route to acetylsilanes. A comparison of the relative efficiency of the transmetalation of (α-methoxyvinyl)- and vinyltin compounds is reported. © 1982, American Chemical Society. All rights reserved.