6240-49-9Relevant academic research and scientific papers
Dispersion-Controlled Regioselective Acid-Catalyzed Intramolecular Hydroindolation of cis-Methindolylstyrenes to Access Tetrahydrobenzo[ cd]indoles
Cai, Xiao,Tohti, Anargul,Ramirez, Cristian,Harb, Hassan,Fettinger, James C.,Hratchian, Hrant P.,Stokes, Benjamin J.
, p. 1574 - 1577 (2019/03/20)
Readily prepared cis-β-(α′,α′-dimethyl)-4′-methindolylstyrenes undergo acid-catalyzed intramolecular hydroindolation to afford tetrahydrobenzo[cd]indoles. Our experimental and computational investigations suggest that dispersive interactions between the indole and styrene preorganize substrates such that 6-membered ring formation is preferred, apparently via concerted protonation and C-C bond formation. When dispersion is attenuated (by a substituent or heteroatom), regioselectivity erodes and competing oligomerization predominates for cis substrates. Similarly, all trans-configured substrates that we evaluated failed to cyclize efficiently.
Direct Synthesis of Indanes via Iron-Catalyzed Dehydrative Coupling/Friedel–Crafts Cyclization of Two Different Alcohols
Sai, Masahiro
supporting information, p. 1102 - 1106 (2019/02/14)
We report herein a novel iron-catalyzed cascade dehydrative coupling/Friedel–Crafts cyclization of two different alcohols, providing a variety of indanes, which are ubiquitous substructures found in natural products, pharmaceuticals, and functional materi
Br?nsted Acid-Catalyzed Intramolecular Hydroarylation of β-Benzylstyrenes
Cai, Xiao,Keshavarz, Amir,Omaque, Justin D.,Stokes, Benjamin J.
supporting information, p. 2626 - 2629 (2017/05/24)
Using triphenylmethylium tetrakis(pentafluorophenyl)borate as a convenient Br?nsted acid precatalyst, β-(α,α-dimethylbenzyl)styrenes are shown to cyclize efficiently to afford a variety of new indanes that possess a benzylic quaternary center. The geminal dimethyl-containing quaternary center is proposed to be necessary to arm the substrate for cyclization through steric biasing.
Codimerisation of styrene and α-methylstyrene in the presence of zeolites
Grigor'eva,Bubennov,Khalilov,Kutepov
experimental part, p. 85 - 90 (2012/07/13)
The reaction of styrene with α-methylstyrene has been studied over Y, Beta and ZSM-12 zeolites at 80-120 °C in the presence or absence of chlorobenzene. Homo- and codimers of styrene and α-methylstyrene were the main reaction products. The yield of dimers
Electrophilic additions to styrylsilanes: the effect of changing the ligands on silicon
Brook, Michael A.,Henry, Courtney,Jefferson, Elizabeth,Jueschke, Ralf,Sebastian, Thomas,et al.
, p. 559 - 568 (2007/10/02)
Styrylsilanes readily undergo addition of carbon electrophiles and protons.The products of the reaction depend upon the non-participating substituents on silicon.Thus, while (E)-β-(trimethylsilyl)styrene 4 readily reacts with electrophiles, the reaction products did not contain silicon or new C-C bonds; even in the presence of aryl-substituted carbon electrophiles, the favored reaction was protiodesilylation.In contrast, (E)-β-(trichlorosilyl)styrene 2 did not participate in the reaction with carbon electrophiles or reasonably strong protic acids.However, with triflic acid, 2 cleanly and diastereoselectively dimerized producing after methylation 25, as shown by an X-ray crystal sructure analysis.The simple change of a methyl for a chloro group 3 under the same conditions produced a different diastereomer 19 along with a trimer 21.The reasons for the changes in reaction mechanism are discussed. β-effect / electrophilic addition / styrylsilane / leaving group ability / ligand effect / diastereoselective indane synthesis
The Preparation and Photolysis of (E)-1-Aryl-3-methyl-3-phenylbut-1-enes
Blunt, John W.,Coxon, James M.,Robinson, Ward T.,Schuyt, Helen A.
, p. 565 - 579 (2007/10/02)
Reaction of 2-methyl-2-phenylpropylmagnesium chloride with benzaldehyde in tetrahydrofuran gave, 2,7-dimethyl-2,4,5,7-tetraphenyloctane-4,5-diol as a 1:2 mixture of clear transparent crystalline plates (meso) and needles (+/-), 3-methyl-1,3-diphenylbutan-1-one, benzyl alcohol, 2-methyl-2-phenyl-propane and a low yield of 3-methyl-1,3-diphenylbutan-1-ol.The distinction between the meso- and the (+/-)-diols was unequivocal because the unique space group of the former requires the dimeric molecules to lie about a crystallographic centre of symmetry.The mechanism involved in the formation of the products of the Grignard reaction is examined.By careful choice of reaction conditions a series of 1-aryl-3-methyl-3-phenylbutan-1-ols were prepared.Dehydration of the 1-aryl-3-methyl-3-phenylbutan-1-ols with p-toluenesulfonic acid and a short reaction time gives (E)-1-aryl-3-methyl-3-phenylbut-1-enes but longer reaction times afford 3-aryl-1,1-dimethylindanes.Photolysis of the (E)-1-aryl-3-methyl-3-phenylbut-1-enes affords (Z)-1-aryl-3-methyl-3-phenylbut-1-enes and trans-1-aryl- 3,3-dimethyl-2-phenylcyclopropanes.Extended photolysis gives 4-aryl-2-methyl-3-phenylbut-1-enes via trans-1-aryl-3,3-dimethyl-2-phenylcyclopropane by rupture of the cyclopropyl bond adjacent to the aryl substituent.
