16339-88-1Relevant articles and documents
Dehydrobromination of 1,2-Dibromoethoxyethane Using Various Amine Bases
Stalick, Wayne M.,Khorrami, Ali,Hatton, Kimi S.
, p. 3577 - 3581 (1986)
1,2-Dibromoethoxyethane was treated with a number of basic reagents, mainly tertiary amines, to accomplish dehydrobromination to 1-bromo-2-ethoxyethene, a precursor to an acetaldehyde carbanion equivalent.The yield of this vinyl bromide and the other common byproducts of reaction varied markedly depending on the base and reaction conditions employed.Direct distillation of the product under reduced pressure from a tertiary amine solution was the method of choice, showing little if any effect of temperature and giving reproducible results.Following this procedure, N,N-dimethyldodecylamine was the preffered base for this reaction.This paper presents results of the dehydrobromination reaction using more than 30 different bases and conditions
2-Ethoxyvinyllithiums and diethoxyvinyllithiums: What makes them stable or fragile?
Schlosser, Manfred,Wei, Heng-Xu
, p. 1735 - 1742 (2007/10/03)
The elusive (E)-2-ethoxyvinyllithium can be readily generated in tetrahydrofuran at -75 °C from (E)-1-bromo-2-ethoxyethylene by halogen/metal exchange and subsequently trapped with electrophiles. Alkylation opens a convenient entry to (E)-configurated enethers. (E)-2-Ethoxyvinyllithium decomposes rapidly at -50 °C whereas its (Z)-isomer, which lacks the possibility to eliminate lithium ethoxide in a favorable anti-periplanar process, is stable under the same conditions. (E)-1,2-Diethoxyvinyllithium even sustains reflux temperatures (approximately 75 °C). 2,2-Diethoxyvinyllithium and (Z)-1,2-diethoxyvinyllithium can be conserved at 0 °C although this time loss of alcoholate can occur in the anti-mode. Obviously it matters whether the energy-rich ethoxyacetylene is formed as the elimination product or simple acetylene, as in the case of (E)-2-ethoxyvinyllithium.
