73774-46-6Relevant articles and documents
On the conformational preferences of the dehydrochlorination of α-chlorosulfoxides
Schwan, Adrian L.,Roche, Michael R.,Gallagher, John F.,Ferguson, George
, p. 312 - 324 (2007/10/02)
Several acyclic α-chlorosulfoxides have been shown to undergo a γ-dehydrochlorination upon treatment with LDA.The proposed immediate products of γ-dehydrochlorination, thiirane-S-oxides, are unstable under the basic conditions and react further with the LDA; the isolated products are usually E-alkenes and (or) E-vinyl sulfoxides.Some of the proposed intermediate thiirane-S-oxides, compounds 6, 7, 8, and 18, were synthesized independently and treated with one equivalent of LDA in order to mimic the second step of the overall dehydrochlorination/ring opening sequence.The products obtained from the reactions of compounds 6 and 18 compared favourably with those products which were believed to arise from certain conformations of α-chlorosulfoxides 1kB and 1e, respectively.Tha addition of one equivalent of LDA to 1kA afforded a mixture containing thiirane-S-oxide 8, which is proposed as the immediate product of γ-dehydrochlorination of 1kA.The configurations of 1kB and 1hA were both shown to be threo by X-ray crystallographic studies.Those conformations which are preferred for the dehydrochlorination possess a geometry where the sulfinyl oxygen is anti to any of the substituents of the ring carbons.
REACTIONS OF EPISULPHOXIDES AND EPISULPHIDES WITH ORGANOLITHIUM REAGENTS
Bonini, Bianca F.,Maccagnani, Gaetano,Mazzanti, Germana,Zani, Paolo
, p. 115 - 121 (2007/10/02)
Reactions of aryl-substituted episulphoxides and episulphides with butyl- and phenyllithium, lithium di-isopropyl amide and lithium dimethylcuprate have been examined.The following reaction paths could be observed: a) attack at sulphur leading to olefins with complete retention of configuration at the carbon skeleton; b) attack at proton leading to a vinyl sulphenate in the case of episulphoxides, or to a thiolate anion, in the case of episulphides, trapped as methyl vinyl sulphoxide or methyl vinyl sulphide, respectively; c) attack at carbon, observed only in thereaction of styrene episulphoxide with lithium dimethylcuprate, leading to a saturated sulphenate anion trapped as alkyl methyl sulphoxide.Mechanisms and stereochemistry of these processes are discussed.
Synthesis and Reactions of Phosphoryl-Substituted Sulfines
Porskamp, Pascal A. T. W.,Lammerink, Ben H. M.,Zwanenburg, Binne
, p. 263 - 268 (2007/10/02)
The synthesis of a variety of phosphoryl-substituted sulfines 5 by the reaction of α-silyl carbanions with sulfur dioxide is described.For characterization purposes the prepared sulfines were converted into their cycloadducts 6 with 2,3-dimethyl-1,3-butad
