51567-94-3

Upstream product

• 1950-69-2 toluene-p-sulfonyl bromide 
• 2923-28-6 silver trifluoromethanesulfonate 
• 98-59-9 p-toluenesulfonyl chloride 
• 2232-08-8 N-tosylimidazole 
• 333-27-7 methyl trifluoromethanesulfonate 

Downstream Products

• 120640-46-2 (2R)-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3t-(toluene-4-sulfonyloxy)-chroman 
• 120640-48-4 (2R)-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3c-(toluene-4-sulfonyloxy)-chroman 
• 60520-17-4 toluenesulfonyl [⁽¹⁸⁾F]-fluoride 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 4124-41-8 p-toluenesulfonylanhydride 

Relevant academic research and scientific papers

Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives

The structural core of flavene (2-phenyl-2H-chromene) is commonly found in plant flavonoids, which exhibit a wide range of biological activities and diverse pharmacological profiles (e.g., antioxidant and anticancer activities). Flavonoids have attracted significant interest in medicinal and synthetic chemistry. Substituted flav-3-ene 13 was exclusively synthesized by the stereoselective elimination of the O-mesyl moiety on C-3 of 5,7,3′,4′-tetramethoxyflavan-3-mesylate 12 with 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction of 5,7,3′,4′-tetramethoxyflavan-3-one 15 with ytterbium trifluoromethanesulfonate in methanol afforded a novel 3-O-substituted flav-3-ene derivative (3,5,7,3′,4′-pentamethoxyflav-3-ene) 17. The reduction of 4-(1,3,5-trihydroxybenzene)-5,7,3′,4′-tetra-O-benzylflavan-3-one 19b with hydrogen afforded a new compound: 3-hydroxy-4-(1,3,5-trihydroxybenzene)-5,7,3′,4′-tetrahydroxyflavan-3-en-3-ol 21 in good yield (95%), while the acetylation of 19a and 21 afforded the expected novel flav-3-en-3-acetoxy derivatives 20 (92%) and 22 (90%), respectively.

The Interaction of Arenesulphonyl Chlorides, Aluminium Chloride, and Saturated Alicyclic Hydrocarbons containing at least One Tertiary Hydrogen Atom

Cycloalkanes having at least one tertiary hydrogen react with a mixture of benzenesulphonyl chloride and aluminium chloride in carbon disulphide, with reactivity decreasing in the order cis-decalin ca. cis-hexahydroindane > trans-decalin >/= dicyclohexyl > methylcyclohexane > t-butylcyclohexane > methylcyclopentane.Although hydrogen chloride was evolved and benzenesulphonyl chloride was reduced to benzenesulphinic acid in all the reactions, only cis-decalin, and, to a much smaller extent, dicyclohexyl, gave appreciable amounts of chloro- or dichloro-cycloalkanes.In other reactions the major products were hydrocarbon "dimers" and "trimers" apparently formed by attack by the carbenium ion on cycloalkenes formed in the reaction.Electron-attracting substituents in the arenesulphonyl chloride enhanced the rate of reaction with cis-decalin, and electron-donor substituents retarded the reaction, which appears to proceed via hydride-ion abstraction by the arenesulphonyl halide-aluminium halide "oxonium complex" rather than by the (+) ion.