16192-03-3Relevant academic research and scientific papers
Silver-promoted synthesis of vinyl sulfones from vinyl bromides and sulfonyl hydrazides in water
Zhang, Ge,Fu, Jian-Guo,Zhao, Qian,Zhang, Gui-Shan,Li, Meng-Yao,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information, p. 4688 - 4691 (2020/05/22)
The synthesis of vinyl sulfones via silver-promoted cross-coupling of vinyl bromides with sulfonyl hydrazides was realized. Water was used as the sole solvent. Multisubstituted vinyl sulfones were easily prepared with excellent alkyl group tolerance. A mechanism involving nucleophilic attack of a sulfinate anion was proposed.
Coupling reaction of magnesium alkylidene carbenoids with α-sulfonylallyllithiums: An efficient route to multi-substituted vinylallenes
Kimura, Tsutomu,Kobayashi, Gen,Ishigaki, Masashi,Inumaru, Mio,Sakurada, Jo,Satoh, Tsuyoshi
, p. 3623 - 3632 (2013/02/23)
A variety of vinylallenes were successfully synthesized from 1-chlorovinyl p-tolyl sulfoxides and allyl or vinyl sulfones. Allyl and vinyl sulfones served as α-sulfonylallyllithium sources were prepared from carbonyl compounds in three or four steps in good overall yields. The coupling reaction of α-sulfonylallyllithiums with magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides and isopropylmagnesium chloride, afforded multi-substituted vinylallenes in up to 88% yield. Georg Thieme Verlag KG Stuttgart · New York.
New synthesis of allylidenecyclobutanes by the reaction of cyclobutylmagnesium carbenoids with vinyl sulfones
Ishigaki, Masashi,Inumaru, Mio,Satoh, Tsuyoshi
, p. 5563 - 5566 (2011/11/07)
The reaction of cyclobutylmagnesium carbenoids, which were generated from 1-chlorocyclobutyl p-tolyl sulfoxides with EtMgCl via the sulfoxide-magnesium exchange reaction at low temperature, with carbanions derived from vinyl sulfones with n-BuLi or LDA re
First synthesis, X-ray structure analysis and reactions of alkenyltriphenylbismuthonium salts
Matano, Yoshihiro,Yoshimune, Masanori,Azuma, Nagao,Suzuki, Hitomi
, p. 1971 - 1977 (2007/10/03)
Treatment of triphenylbismuth difluoride with alkenyltrimethylsilanes 1 or trimethylsilyl cyanidealkenyltrialkylstannanes 3 in the presence of boron trifluoride-diethyl ether gave the corresponding alkenyltriphenylbismuthonium tetrafluoroborates 2 in moderate to good yields. An X-ray crystallographic analysis of the salt 2e confirmed the distorted tetrahedral geometry of the central bismuth atom. When treated with a sulfinate 5 or the thiolate 11, the salts 2 readily transferred both the vinyl and phenyl moieties to these nucleophiles to afford the sulfones 7-10 or the sulfides 12, 13, respectively. In the presence of a palladium catalyst, the salt 2e underwent the Heck-type reaction with ethyl acrylate 17 to afford the dienoate 18 and cinnamate 19 in moderate yields. Action of KOBut on the salt 2b yielded p-tolylacetylene 22, while a similar reaction with the salt 2e in the presence of the styrenes 23 gave the cyclopropanes 24. A Hammett study of the latter reaction has suggested a possible involvement of an alkylidenecarbene as the intermediate in these base-promoted reactions.
Addition-Elomonation Reactions of β-Oxygenated Vinyl Sulphines
Giblin, Gerard M. P.,Simpkin, Nigel S.
, p. 207 - 208 (2007/10/02)
Stereoselective reaction of enol pivalate (3) with a variety of higher order organocuprate reagents gives vinyl sulphones in excellent yield.
Convenient Methods for the Preparation of Vinylic and Allylic Sulfones from Alkenes, Haloalkanes, and Aldehydes. Stereochemistry of the Conversion of Vinylic Sulfones to the Corresponding Allylic Sulfones
Inomata, Katsuhiko,Sasaoka, Shin-ichi,Kobayashi, Toshifumi,Tanaka, Yuhji,Igarashi, Susumu,et al.
, p. 1767 - 1780 (2007/10/02)
1- or 2-p-Tolylsulfonyl(=tosyl)-1-alkenes, vinylic sulfones, were regioselectively prepared from 1-alkenes via iodosulfonization or sulfonylmercuration and also from 1-haloalkanes by the homologation or unhomologation methods.The vinylic sulfones thus prepared were further converted to the corresponding allylic sulfones under basic conditions.The stereochemistry of this conversion was discussed.One-carbon homologated allylic sulfones were directly obtained from aldehydes in good yields by the reaction with diethyl phenylsulfonylmethylphosphonate and 1,8-diazabicycloundec-7-ene (DBU) under mild conditions.
CONVENIENT METHODS FOR THE PREPARATION OF VINYLIC AND ALLYLIC SULFONES FROM ALKENES
Inomata, Katsuhiko,Kobayashi, Toshifumi,Sasaoka, Shin-ichi,Kinoshita, Hideki,Kotake, Hiroshi
, p. 289 - 292 (2007/10/02)
1 or 2-p-Toluenesulfonyl(=tosyl)-1-alkenes were regioselectively prepared from 1-alkenes via iodosulfonization or sulfonylmercuration, respectively.Conversion of 1-tosyl-1-alkenes to the corresponding allylic sulfones, 1-tosyl-2-alkenes, was achieved by t
Organic synthesis with sulphones no. XXXIV. Uncatalysed addition versus nickel catalysed coupling reaction of vinylic sulfones with Grignard reagents. A stereoselective synthesis of olefins and dienes
Fabre, Jean-Luc,Julia, Marc,Verpeaux, Jean-Noel
, p. 762 - 771 (2007/10/02)
Grignard reagents undergo Michael addition to vinylic sulfones.With a β-β-disubstituted vinylic sulfone an unexpected dimer is obtained.Under nickel catalysis methyl, aryl and alkenyl Grignard reagents displace the sulfonyl group of the readily available α,β-unsaturated sulfones.Methyl, resp. phenyl substituted olefins or conjugated dienes are formed.Under appropriate conditions the reaction proceeds with complete retention of configuration.
ARYL VINYL SULFONES AS THIOL PROTECTIVE GROUP
Kuroki, Yoshiaki,Lett, Robert
, p. 197 - 200 (2007/10/02)
Phenyl vinyl sulfone and p-tolyl isobutenyl sulfone are convenient reagents for protecting SH groups via the Michael adduct.Protection and deprotection can be achieved in high yields under mild basic conditions, in protic or aprotic solvents.
