69747-26-8Relevant articles and documents
Conversion of alcohols to alkyl aryl sulfides by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite
Kuroda, Kiichi,Maruyama, Yuji,Hayashi, Yujiro,Mukaiyama, Teruaki
experimental part, p. 381 - 392 (2009/06/28)
Preparation of alkyl aryl sulfides from alcohols and arenethiols such as 2-sulfanyl-1,3-benzothiazole (BtzSH) is described by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite (PhOPPh 2) and benzoquinone derivatives or azide compounds. This reaction proceeds under mild and neutral conditions and is applicable to the thioetherification of various alcohols in which the chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides with almost complete inversion of configuration.
A convenient method for the preparation of alkyl aryl sulfides from alcohols and (chloromethylene)dimethylammonium chloride
Kawano, Yoshikazu,Kaneko, Nobuya,Mukaiyama, Teruaki
, p. 1612 - 1613 (2007/10/03)
(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent), prepared easily from DMF and oxalyl chloride, works as an efficient condensation reagent for the thioetherification of alcohols in one-pot under mild conditions. Various alcohols are successively converted into the corresponding sulfides with inversion of configurations in moderate to high yields. Copyright
Stereochemistry of direct olefin formation from carbonyl compounds and lithiated heterocyclic sulfones
Baudin, J. B.,Hareau, G.,Julia, S. A.,Lorne, R.,Ruel, O.
, p. 856 - 878 (2007/10/02)
The conditions for the title reaction were studied for the 2-benzothiazole and 2-pyridine series and for some examples in the 2-pyrimidine series.The olefin preparations were generally observed to be more efficient for 2-BT-sulfone systems.From the data of the hundred cases studied, it can be concluded that (E)-olefins are obtained: (i) from saturated BT-sulfones and aromatic aldehydes; and (ii) from benzylic BT-sulfones and branched saturated aldehydes (isobutyraldehyde, pivalaldehyde) or α,β-ethylenic or aromatic aldehydes. (Z)-olefins arise: (i) fom propargylic BT-sulfones and saturated or aromatic aldehydes; and (ii) from allylic or benzylic Pyr-sulfones and saturated aldehydes.Possible mechanisms for this new olefination procedure were examined. - heteroaromatic sulfones, organolithium derivatives, intramolecular ipso reactions, stereochemistry, elimination, olefination.