77197-72-9Relevant academic research and scientific papers
Direct generation of lithium homoenolates from 3-aryl α,β-unsaturated ketones or esters by an arene-catalysed lithiation: Synthesis of substituted tetrahydrofurans and γ-butyrolactones
Alonso, Emma,Ramon, Diego J.,Yus, Miguel
, p. 2641 - 2652 (2007/10/03)
The reaction of α,β-unsaturated ketones 1 with an excess of lithium powder, a catalytic amount of naphthalene (4%) and different carbonyl compounds in the presence of boron trifluoride in THF at -78-0°C yields, after treatment with silyl nucleophile and final hydrolysis, the expected substituted tetrahydrofurans 5. Similar methodology applied to β-aryl acrylic esters 6, but without using boron trifluoride or silyl reagents yields the corresponding lactones 7.
Synthesis of γ-Lactones and 3-Alkylidene-1-indanones
Jalander, Lars,Broms, Merete
, p. 371 - 376 (2007/10/02)
γ-Lactones are formed in high yields in the reactions of (E)-3-alkyl-3-phenylpropenoic acids in concentrated sulfuric acid if the alkyl groups contain a tertiary γ-hydrogen.If the alkyl groups bear secondary γ-hydrogens 3-alkylidene-1-indanones are formed almost exclusively.Reaction mechanisms for the cyclizations are discussed on the basis of deuteration experiments.
REACTION OF DI(BROMOMAGNESIO)ALKANES WITH UNSYMMETRICALLY SUBSTITUTED CYCLIC ANHYDRIDES
Canonne, Persephone,Lemay, Gilles,Belanger, Denis
, p. 4167 - 4170 (2007/10/02)
Alkylated γ-spirolactones were prepared in one-step reactions in high yields from butane-1,4-diyl and pentane-1,5 diyldimagnesium dibromides and substituted cyclic anhydrides in tetrahydrofuran.In the light of experimental findings electronic and steric factors influence the regiospecificity of this reaction.
