73774-46-6Relevant academic research and scientific papers
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.
The One-pot Generation and Ring Opening of Alkyl and Aryl Thiirane-S-oxides
Schwan, Adrian L.,Wilson, David A.
, p. 5897 - 5900 (2007/10/02)
Base induced dehydrochlorination of acyclic α-chlorosulfoxides affords thiirane-S-oxides which react further under the alkaline reaction conditions.
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
STEREOCHEMISTRY OF ORGANIC SULPHUR COMPOUNDS. Part 13. CONFIGURATIONAL ASSIGNMENT OF DIASTEREOISOMERS OF 2-METHYLSULPHINYL-1,2-DIPHENYLETHANOL AND THEIR O-METHYL AND O-ACETYL DERIVATIVES
Brunet, E.,Ruano, J. L. Garcia,Martinez, M. C.,Rodrigez, J. H.,Alcudia, F.
, p. 2023 - 2034 (2007/10/02)
The synthesis, isolation and conformational analysis of the diastereomeric 2-methylsulphinyl-1,2-diphenylethanol and its O-methyl and O-acetyl derivatives are reported.Chemical correlations and the study of the influence of solvent polarity changes on the coupling constants have permitted the configurational assignment.Lanthanide shift reagents have been used also to this effect.The role of hydrogen bonding in the hydroxysulphoxides has been evaluated in diluted solutions by IR and NMR spectroscopy.A donor-acceptor interaction between oxygen and sulphur has been invoked to explain the differences in conformational behaviuor between epimeric sulphoxides at sulphur atom.
