91358-89-3Relevant academic research and scientific papers
Organic reactions in ionic liquids: A new method for the synthesis of alkyl aryl sulfones by alkylation of sodium arenesulfinates with unactivated alkyl chlorides
Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
, p. 4031 - 4035 (2007/10/03)
A new method is reported for the synthesis of alkyl aryl sulfones by alkylation of sodium arenesulfinates with unactivated alkyl chlorides using ionic liquid based on 1-butyl-3-methylimidazolium tetrafluoroborate (BmimBF 4) mixed with water (2:1) as reaction media. The ionic liquid can be reused and the procedure gives the sulfones in moderate yields.
Sulfonylation of Organometallic Reagents with Arenesulfonyl Fluorides: A Simple One-Step Synthesis of Sulfones
Frye, Leah L.,Sullivan, Eileen L.,Cusack, Kevin P.,Funaro, John M.
, p. 697 - 701 (2007/10/02)
Sulfonylation of organometallic reagents was accomplished with arenesulfonyl fluorides to provide a wide variety of alkylaryl- and diaryl sulfones.Organolithium and diorganocopper lithium reagents react smoothly with arenesulfonyl fluorides to give sulfones in high yields.Alkyl Grignard reagents often lead to mixtures of monosulfonylated and disulfonylated products.However, allylmagnesium chloride and phenylmagnesium chloride provide the corresponding sulfones in excellent yields.Organocopper reagents were also found to yield sulfones upon treatment with arenesulfonyl fluorides.By utilizing this methodology, synthetically useful alkyl, (trimethylsilyl)methyl, and allyl sulfones are easily prepared in high yields.
Substitution Reactions of Organocuprates with β-(Phenylseleno)vinyl Sulfones Derived from the Selenosulfonation of Acetylenes. A Convenient and Stereospecific Preparation of Vinyl Sulfones and Olefins from Acetylenes
Back, Thomas G.,Collins, Scott,Krishna, M. Vijaya,Law, Kwok-Wai
, p. 4258 - 4264 (2007/10/02)
The free-radical selenosulfonation of acetylenes affords β-selenovinyl sulfones 1 which undergo substitution of the selenium moiety with organocuprates to provide a convenient and stereospecific preparation of vinyl sulfones 2 and therefore ultimately of
SELENOSULFONATION OF ACETYLENES. SUBSTITUTION REACTIONS OF β-(PHENYLSELENO)VINYL SULFONES WITH ORGANOCUPRATES
Back, Thomas G.,Collins, Scott,Law, Kwok-Wai
, p. 1689 - 1692 (2007/10/02)
β-(Phenylseleno)vinyl sulfones are readily available from the selenosulfonation of acetylenes and undergo efficient, stereoselective substitution of the phenylseleno moiety by the alkyl group of alkyl (phenylseleno)cuprates.
MODERN FRIEDEL-CRAFTS CHEMISTRY. XI. CYCLIZATION OF ARYL HALOALKYL SULFONES, ARYLSULFONYLACYL CHLORIDES AND THEIR CORRESPONDING SULFIDES
Abdel-Wahab, Aboel-Magd A.,El-Khawaga, Ahmed M.,El-Zohry, Maher F.,Khalaf, Ali A.
, p. 31 - 44 (2007/10/02)
The sulfone group deactivation for cyclialkylation and cycliacylation reactions in the presence of Friedel-Crafts catalysts was demonstrated in a number of aryl chloroalkylsulfones (1-8) and arylsulfonylacyl chlorides (17a-22a), respectively.As expected, the corresponding arylchloroalkyl sulfides (9-16) and arylmercaptoacyl chlorides (13a-28a) underwent ring-closure reaction in most cases under the same conditions.The ease of cyclization was governed by the ring size, the stability of the attacking carbocation and the nucleophilicity of the aryl moiety.Also, the behaviour of benzyl sulfones (29, 31a, and 32a) and sulfides (33, 34a and 36a) was inconsistent.Noteworthy, the Friedel-Crafts cyclization reaction is thus considered an accessible method for the synthesis of compounds 37-41 and 45, 51.
