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Issue 4, 1989
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Synthesis of mono and gem-dihalogeno-olefins from carbonyl compounds and in situ generated lithium carbenoids

Abstract

The treatment of carbonyl compounds (5) with dihalogenomethane and lithium dicyclohexylamide at –78 °C leads after acid hydrolysis to the crude alcohols (6), which by silylation with trimethylchlorosilane–hexamethyldisilazane–pyridine affords the crude silylated alcohols (7); final treatment of compound (7) with lithium di-isopropylamide or butyl-lithium (when one of the halogens is bromine) at low temperature gives the corresponding di- or mono-halogenated olefins (8) or (9), respectively, through a sole β-elimination process.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1989, 691-694
Article type
Paper

Synthesis of mono and gem-dihalogeno-olefins from carbonyl compounds and in situ generated lithium carbenoids

J. Barluenga, J. L. Fernández-Simón, J. M. Concellón and M. Yus, J. Chem. Soc., Perkin Trans. 1, 1989, 691 DOI: 10.1039/P19890000691

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