104130-08-7Relevant academic research and scientific papers
Three-Component Radical Condensations Involving Benzoylmethyl Radicals, Alkenes, and Diphenyl Disulfide
Russell, Glen A.,Kulkarni, Shekhar V.
, p. 2678 - 2685 (2007/10/02)
Acyl-substituted methyl radicals (RCOCH2.; R = H, Me, Ph), generated by photolysis of RCOCH2HgCl, add to alkenes, enol ethers, or vinyl sulfides to give adduct radicals that are readily trapped by PhSSPh to yield a three-component condensation product.The presence of an alkali metal carbonate is crucial in preventing side reactions resulting in the conversion of the mercurial to RCOCH3 by PhSH formed in the photolysis.
A Comparison of the Reactions of lithium with α,β-Unsaturated Ketones and Those of Other Acyl Anion Equivalents Containing Sulfur
Ager, David J.,East, Michael B.
, p. 3983 - 3992 (2007/10/02)
The factors influencing the site of attack of lithium (1) with enones were investigated.Cyclohexenone (2) was chosen as a model compound, and conjugate addition occurred in THF-HMPA or DME; this mode of addition was also promoted by a potassium counterion.When the reaction was carried out with other enones, conjugate addition in THF-HMPA or DME was only observed if the β-position or the α,β-unsaturated ketone was not disubstituted. 1,4-Addition of 1 could be accomplished by preparation of the cuprate.The use of this approach was illustrated by a preparation of 4,4-dimethylcyclopent-2-en-1-one (28).For determination of the influence of DME on the regiochemical control of the addition of other sulfur-containing anions to enones, the study was extended to the anions derived from 1,3-dithian (29), bis(phenylthio)methane (30), bis(phenylthio)(trimethylsilyl)methane (35), and bis(trimethylsilyl)(phenylthio)methane (36).With these anions, DME did not promote conjugate addition to any significant extent.
