53097-28-2Relevant articles and documents
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.
The Formation of Vinyl Sulfides by the Cleavage of the Carbon-Sulfur Bond in Dithioacetals with CuCl2
Oida, Tatsuo,Tanimoto, Shigeo,Ikehira, Hideyuki,Okano, Masaya
, p. 959 - 960 (2007/10/02)
The elimination of arene- and alkanethiol from diaryl and dialkyl dithioacetals, in the presence of copper(I) or copper(II) salt plus tertiary amine, to produce the corresponding aryl and alkyl vinyl sulfides, respectively, has been studied.The employment of a combination of 2 mol equiv. of CuCl2 and 2 mol equiv. of N,N-diisopropylethylamine is most favorable.
