64346-07-2Relevant academic research and scientific papers
Arylbis(arylthio)sulfonium Salts as Reagents for the Synthesis of 2-Deoxy-β-glycosides
Grewal, Gurmit,Kaila, Neelu,Franck, Richard W.
, p. 2084 - 2092 (2007/10/02)
The title sulfonium salts undergo electrophilic addition to glycals in the presence of alcohols to form principally β-glycosides.A substituent effect study has shown that the reagent with a p-tolylthio group is the most face-selective.By variation of the alcohol nucleophile, it has been shown that face selectivity is also dependent on the structure of the nucleophile.One instance of double diastereodifferentiation was uncovered when the racemic alcohol 23.5 was used in a reaction with tribenzyl glucal 22.1.The effect of glycal substitution on the face selectivity has led to the postulation of a heretofore unrecognized and still unexplained stereoelectronic effect.
Hydrozirconation of Thioketones. A Simple, Convenient Entry into a Variety of Organosulfur Compounds. An Intersting Ether Synthesis
Laycock, David E.,Alper, Howard
, p. 289 - 293 (2007/10/02)
Aromatic and aliphatic thioketones undergo hydrozirconation at room temperature with (C5H5)2Zr(H)Cl to give sulfur-zirconium compounds, R2CHSZr(Cl)(C5H5)2.Cleavage of the latter by bromine or N-bromosuccinimide affords sulfenyl bromides, acid chlorides give thioesters, methyloxalyl chloride gives a thiooxalate, methyl vinyl ketone results in the formation of the β-keto sulfide, and carbonylation followed by bromination in alcohol affords the ether.Yery mild conditions are utilized for all of these reactions.Mechanisms are proposed for the interesting ether synthesis.
