15543-64-3Relevant academic research and scientific papers
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 (2001)
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.
Synthesis of a comprehensive polyprenol library for the evaluation of bacterial enzyme lipid substrate specificity
Wu, Baolin,Woodward, Robert,Wen, Liuqing,Wang, Xuan,Zhao, Guohui,Wang, Peng George
, p. 8162 - 8173 (2014/01/06)
Polyprenols, a universal class of glycan-carrier lipids, play important roles in glycan biosynthesis in wide variety of living organisms. The chemical synthesis of natural polyisoprenols such as undecaprenol and dolichols, and even more so the synthesis o
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.
A synthesis of the pseudopterosin A-F aglycone
Cooksey, John P.,Kocienski, Philip J.,Schmidt, Arndt W.,Snaddon, Thomas N.,Kilner, Colin A.
supporting information, p. 2779 - 2785,7 (2020/07/31)
The synthesis of the pseudopterosin A-F aglycone from 3-methylcatechol features (a) the use of asymmetric Ireland-Claisen and aryl Claisen rearrangements to install three of the four stereocentres present in the molecule and (b) an A→AB→ABC annulation strategy using ring-closing metathesis and cationic cyclisation reactions as the key steps.
Studies on taxadiene synthase: Interception of the cyclization cascade at the isocembrene stage with GGPP analogues
Chow, Siew Yin,Williams, Howard J.,Huang, Qiulong,Nanda, Samik,Scott, A. Ian
, p. 9997 - 10003 (2007/10/03)
The cyclization of GGPP to taxadiene, catalyzed by taxadiene synthase, has been suggested to proceed through a series of monocyclic isocembrenyl- and bicyclic verticillyl-carbocationic intermediary stages. A set of GGPP analogues with abolished or perturbed π-nucleophilicity at the Δ10 double bond (GGPP numbering) was synthesized and incubated with taxadiene synthase to intercept the cyclization cascade at the monocyclic stage. Each analogue was transformed by taxadiene synthase in vitro to hydrocarbon products in varying yields, and the structures of the major product in each reaction were solved by GCEIMS and one- and two-dimensional (1H and 13C) NMR and found to be 14-membered monocyclic isocembrenyl diterpenes, indicating that the first C-C bond formation catalyzed by taxadiene synthase could be uncoupled from the other subsequent bond formation events by using suitably designed substrate analogues. The formation and isolation of these isocembrenyl diterpene products using taxadiene synthase supports proposals that the isocembrenyl cation is an intermediate in the cyclization of GGPP to taxadiene.
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.
A NEW GENERAL SYNTHESIS OF SULFONES FROM ALKYL OR ARYL HALIDES AND p-TOLUENESULFONHYDRAZIDE
Ballini, Roberto,Marcantoni, Enrico,Petrini, Marino
, p. 6791 - 6798 (2007/10/02)
Here we report the utilization of commercially available p-toluenesulfonhydrazide as a new nucleophilic reagent in displacement reactions with suitable halides for an improved, general synthesis of sulfones.Good results are obtained with primary, secondary, allylic, benzylic, and aromatic halides activated by withdrawing groups.
Coupling Reaction of Allyl Sulfones Using Sodium Hydroxide in Liquid Ammonia
Takikawa, Yuji,Osanai, Kimiko,Sasaki, Satoshi,Shimada, Kazuaki
, p. 1939 - 1942 (2007/10/02)
Vinylcyclopropane derivatives containing two isomers were respectively obtained in good yields in the reactions of 3-methyl-2-butenyl, geranyl, and neryl p-tolyl sulfones with NaOH in liquid ammonia.On the other hand, the reaction with crotyl p-tolyl sulfone gave 2-ethyl-1,3-di-p-toluenesulfonylpropane in good yield.
Organic Synthesis with sulfones. XLI. Nucleophilic substitution of allylic sulfones
Julia, Marc,Nel, Maurice,Uguen, Daniel
, p. 487 - 492 (2007/10/02)
The sulfonyl group in allylic sulfones can be displaced by a variety of nucleophiles.The reaction is particularly easy with tertiary sulfones, i.e. bearing no hydrogen atoms at the α-position.Lewis acids catalyse the displacement reaction.
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
