Reactivity of α,β-unsaturated acetals with electrophiles in the presence of organolithium–potassium reagents
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 14,p. 1032-1033
- https://doi.org/10.1039/c39920001032
Abstract
2-Propenyl- and 2-(2-methylpropenyl)-1,3-dioxane react with 2 equiv. of sec-butyllithium complexed with potassium tert-butoxide in tetrahydrofuran (THF) at –95 °C undergoing a 1,4 eliminative ring fission with subsequent proton abstraction at the α vinyl site of the enol ethers produced; carbanions obtained undergo substitution and addition reactions with electrophiles.Keywords
This publication has 7 references indexed in Scilit:
- Reactions of oxathio-substituted crotyllithium with alkyl halides and carbonyl compounds. An example of an ambident nucleophileTetrahedron, 1992
- Regioselectivity in lithium, sodium and potassium chloroallyl systems. An ab initio-theoretical and experimental studyTetrahedron, 1991
- Reactivity of α,β-unsaturated acetals and ketals toward organolithium reagents in pentaneTetrahedron Letters, 1984
- Facile S N? reaction of alkyl-lithiums with 2-vinyl-1,3-dioxaneJournal of the Chemical Society, Chemical Communications, 1984
- New functional allylic lithium reagents: gem-dialkoxyallyllithium reagents: a useful route to β-silyl- and β-stannylpropionate estersJournal of Organometallic Chemistry, 1980
- 2-Alkenyl anions and their surprising endo preference. Facile and extreme stereocontrol over carbon-carbon linking reactions with organometallics of the allyl typeJournal of the American Chemical Society, 1976
- Preparation of organopotassium compoundsJournal of Organometallic Chemistry, 1971