68978-36-9Relevant academic research and scientific papers
SO2 conversion to sulfones: Development and mechanistic insights of a sulfonylative Hiyama cross-coupling
Adenot, Aurélien,Char, Jo?lle,Von Wolff, Niklas,Lefèvre, Guillaume,Anthore-Dalion, Lucile,Cantat, Thibault
supporting information, p. 12924 - 12927 (2019/11/05)
A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion.
Aluminum chloride-iron promoted coupling of sulfonyl chlorides with alkyl halides in aqueous media
Saikia, Promod,Laskar, Dhrubojyoti D.,Prajapati, Dipak,Sandhu, Jagir S.
, p. 512 - 513 (2007/10/03)
A simple and inexpensive procedure for the coupling of sulfonyl chlorides and alkyl halides with aluminum chloride-iron system at ambient temperature in high yield is achieved in aqueous media.
Bi or Cd-induced coupling of sulfonyl chlorides with allylic halides. A simple synthesis of allylic sulfones
Baruah, Mukulesh,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S.
, p. 1083 - 1084 (2007/10/03)
The bismuth or cadmium-catalyzed coupling reaction between aryl and alkyl sulfonyl chlorides and allylic halides proceeds smoothly to provide excellent yields of allylic sulfones at ambient temperature.
SH2' Type Reactions of Arenesulfonyl Chlorides with Allylic Compounds Catalyzed by a Ruthenium(II) Complex
Kamigata, Nobumasa,Ishii, Kimiko,Ohtsuka, Takeshi,Matsuyama, Haruo
, p. 3479 - 3481 (2007/10/02)
In the presence of a catalytic amount of dichlorotris(triphenylphosphine)ruthenium(II), the reactions of arenesulfonyl chlorides with allyl phenyl sulfide and allyl phenyl selenide proceeded smoothly to give allyl phenyl sulfone in high yield as well as the corresponding diphenyl disulfide or diphenyl diselenide.An SH2'-type mechanism involving the arenesulfonyl radical is proposed.
Palladium-Catalyzed Allylic Sulfinate-Sulfone Rearrangements
Hiroi, Kunio,Makino, Kunitaka
, p. 1727 - 1737 (2007/10/02)
Upon treatment with a zero-valent palladium catalyst, tetrakis(triphenylphosphine)palladium, in tetrahydrofuran under mild conditions allylic p-toluenesulfinates underwent α- or γ-rearrangements of the sulfonyl group via ionic intermediates to give allylic sulfones.The regiochemistry of the rearrangements depends on the character of the intermediary allylic cationic carbons generated and the steric hindrance involved therein.Keywords - allylic sulfinate; allylic sulfone; palladium catalyst; sulfinate-sulfone rearrangement; regiochemistry; tetrakis(triphenylphosphine)palladium.
Preparation of some Allylic Sulphones; Base-catalysed Isomerisation and Deuteriation of Cyclohex-2-enyl p-Tolyl Sulphones
Knight, Derek J.,Lin, Peter,Russell, Simon T.,Whitham, Gordon H.
, p. 2701 - 2706 (2007/10/02)
A summary of the methods used in the preparation of a range of allylic sulphones is given.In the case of the conformationally biased sulphones (5) and (6) stereospecific preparation from the cis- and trans-5-t-butylcyclohex-2-en-1-ols was achieved by rear
Rearrangement of Some Allylic Sulphinate Esters to Allylic Sulphones. Ion-pair and Sigmatropic Shift Mechanisms
Knight, Derek J.,Whitham, Gordon H.,Williams, Jonathan G.
, p. 2149 - 2152 (2007/10/02)
The mechanism of rearrangement of a number of allylic sulphinate esters to the corresponding allylic sulphones on heating in formamide has been investigated as a function of substrate structure.Simple systems such as crotyl and α-methylallyl-sulphinate ap
HOMOLYTIC DISPLACEMENT AT CARBON. X. TOLUENESULPHONYL IODIDE AS A SOURCE OF TOLUENESULPHONYL RADICALS FOR THE FORMATION OF ALLYL-, BENZYL-, CYCLOPROPYLCARBINYL-, SPIROCYCLOPROPYLCYCLOALKYL-, BICYCLOALKYL-, AND BICYCLOALKYL-4-TOLYLSULPHONES FROM ORGANOCOBALOXIMES
Ashcroft, Martyn R.,Bougeard, Peter,Bury, Adrian,Cooksey, Christopher J.,Johnson, Michael D.
, p. 403 - 416 (2007/10/02)
4-Toluenesulphonyl iodide reacts thermally at alkylsulphone.Spiro- and bicyclo-alkyl compounds are also formed with other free radical precursors.The reactions are believed to take place through a chain mechanism in which cobaloxime(II), present adventitiously or formed by partial homolysis of the substrate, abstracts iodine from the toluenesulphonyl iodide to give the toluenesulphonyl radical, which attacks the organic ligand of the cobaloxime, preferably at the terminal olefinic carbon, thereby displacing cobaloxime(II) and giving the observed organic product.
Studies on Chiral Organo-Sulfur Compounds. II. Stereochemistry of Thermal Chiral Allyl Sulfinate-Sulfone Rearrangements
Hiroi, Kunio,Kitayama, Ryuichi,Sato, Shuko
, p. 2628 - 2638 (2007/10/02)
A highly efficient and general synthetic route to optically active sulfinates by the stereospecific boron trifluoride etherate-catalyzed esterification of sulfinamides was developed.Dramatic solvent effects were observed in the thermal transformation of allyl sulfinate derivatives to sulfones.Heating of chiral trans- and cis-allyl sulfinates, (S)-(-)-3a,c,e and (S)-(-)-3b,d,f, in N,N-dimethylformamide at 90-120 deg C provided chiral sulfones (S)-(+)- and (R)-(-)-5,6,7 in good yields, respectively, with exceedingly high stereospecificity. Keywords - asymmetric transfer; stereospecificity; chiral allyl sulfinate; chiral allyl sulfone; boron trifluoride etherate; thermolysis
SYNTHESE A L'AIDE DE SULFONE-XXV. SUBSTITUTION SUR DES SULFONES: L'ANION PHENYLSULFINATE COMME GROUPE PARTANT DANS LA SUBSTITUTION DES SULFONES ALLYLIQUES PAR DES REACTIFS DE GRIGNARD EN PRESENCE DE SELS DE CUIVRE
Julia, Marc,Righini-Tapie, Anne,Verpeaux, Jean-Noel
, p. 3283 - 3288 (2007/10/02)
Displacement reactions of the sulphinate anion from sulfones by Grignard reagents with copper catalysis take place readily with allylic sulphones.The regio chemistry and stereochemistry of the reaction are discussed.
