15289-15-3Relevant academic research and scientific papers
AlCl3-mediated aldol cyclocondensation of 1,6- and 1,7-diones to cyclopentene and cyclohexene derivatives
Miyahara, Yuji,Ito, Yoshio N.
, p. 6801 - 6807 (2014/08/18)
Exactly 1/3 mol of AlCl3 is sufficient to cyclize 1 mol of 1,?-dibenzoylbutane (or pentane) to a cyclopentenone (or hexenone) derivative in high yield at room temperature in 40 min to several hours. This condensation is driven by removing elements of water as HCl and Al(OH)3, and the product enones are exclusively unconjugated, unlike the base-catalyzed condensations providing thermodynamically more stable conjugated enones.
Electrophilic Substitution of β,γ-Unsaturated Esters and Ketones using Phenyl Vinyl Sulphoxide as a Vinyl Cation Synthon
Veen, Reinout H. van der,Cerfontain, Hans
, p. 661 - 668 (2007/10/02)
This paper describes a number of examples in which phenyl vinyl sulphoxide is used as a vinyl cation equivalent to react with sterically hindered, charge-stabilized anions derived from α-alkyl-β,γ-unsaturated ketones and esters.With the β,γ-enones (4), (7), and (22), the Michael addition proved to proceed effectively upon using a catalytic amount of base and t-butyl alcohol as solvent.Pyrolysis of the addition product and subsequent distillation in vacuo afforded the β,γ;β'γ'-dienones in good yields.The α,β-enone (1) and the β,γ-unsaturated esters (10) and (15) reactions were performed using sodium hydride as base in benzene.Pyrolysis of the Michael addition products (2), (11), and (16) yielded the β,γ;β'γ'-dienone (3) and the β,γ;β'γ'-unsaturated esters (12) and (17).The β,γ;β'γ'-dienones (13), (14), (18), and (19) have been obtained by subsequent saponification of the two esters, conversion of the resulting carboxylic acids into the corresponding acyl chlorides, and reaction of the latter with dimethyl- or diphenyl-cuprate.
