37634-53-0Relevant academic research and scientific papers
Pd-Catalyzed Nazarov-Type Cyclization: Application in the Total Synthesis of β-Diasarone and Other Complex Cyclopentanoids
Singh, Bara,Bankar, Siddheshwar K.,Ramasastry
, p. 1043 - 1048 (2022/02/05)
We describe the palladium-catalyzed Nazarov-type cyclization of easily accessible (hetero)arylallyl acetates to pentannulated (hetero)arenes. This method provides ready access to various types of bi-, tri-, tetra-, and pentacyclic cyclopentanoids under ne
Investigation of substituent effects on the selectivity of 4π-electrocyclization of 1,3-diarylallylic cations for the formation of highly substituted indenes
Smith, Chris D.,Rosocha, Gregory,Mui, Leo,Batey, Robert A.
supporting information; experimental part, p. 4716 - 4727 (2010/09/05)
(Figure Presented) Differentially substituted 1,3-diaryl-substituted allylic cations generated by ionization of the corresponding allylic alcohols in the presence of a Lewis acid undergo chemoselective and regioselective electrocyclization reactions to generate 1-aryl-1H-indenes. Electrocyclization only occurs for allylic cations bearing a 2-substituent, with 2-ester and 2-alkyl substituents both tolerated. In general, the presence of electron-withdrawing substituents deactivates the ring and disfavors cyclization. In contrast, the selectivity of cyclization of systems containing electron-donating substituents depends on the nature and position of the electron-donating group. Electron-donating substituents at the meta position particularly favor cyclization. There was no obvious correlation of cyclization selectivity with calculated electron densities as has been suggested for electrophilic aromatic substitution reactions. However, the calculated selectivities determined by a gas-phase (B3LYP/6-31G* + ZPVE) comparison of the relative rates of cyclization were in remarkably good agreement with the observed selectivities. Calculated transition-state structures for cyclization are consistent with a cationic π4a conrotatory electrocyclization mechanism. In some cases involving more electron-deficient systems, the initially formed 1H-indene underwent subsequent alkene isomerization to the 3H-indene. In one example, an unusual dimerization reaction occurred to give a cyclopenta[a]indene via an unusual formal cationic 2π+2π cycloaddition of the allylic cation with the intermediate indene.
Efficient synthesis of indenes by FeCl3·6H2O-catalyzed intramolecular Friedel-Crafts reaction of aryl-substituted allylic alcohols
Wang, Jialiang,Zhang, Lixin,Jing, Yufeng,Huang, Wen,Zhou, Xigeng
experimental part, p. 4978 - 4982 (2009/12/01)
An efficient procedure for the synthesis of substituted indenes through the FeCl3·6H2O-catalyzed intramolecular Friedel-Crafts cyclization of aryl-substituted allylic alcohols has been developed. This method features the easily avail
Ruthenium-catalyzed cyclization of alkyne-epoxide functionalities through alternation of the substituent and structural skeleton of epoxides
Ming-Yuan, Lin,Madhushaw, Reniguntala J.,Liu, Rai-Shung
, p. 7700 - 7704 (2007/10/03)
Treatment of 1-(o-ethynylphenyl)-2-alkyl-2-aryl epoxides with TpRuPPh 3(CH3CN)2PF6 catalyst (10 mol %) in hot toluene (100 °C, 12 h) led to an atypical cyclization and gave 1-aryl-2-alkyl-1H-indene derivatives a
Modern Friedel-Crafts chemistry. Part-26. A facile synthesis of trans-2-methyl-1-phenylindan via rearranged intramolecular cyclialkylation of 1,2-diphenyl-2-methyl-2-propanol under Friedel-Crafts conditions
Khalaf, Ali A.,Albar, Hassan A.
, p. 518 - 521 (2007/10/03)
1,2-Diphenyl-2-methyl-2-propanol (1) was prepared by two alternative Grignard methods. Treatment of 1 with AlCl3, AlCl3/CH 3NO2 or K10 clay catalyst in benzene, toluene of dichloromethane solvent at varying temperatures for varying times gave trans-2-methyl-1-phenylindan (4) as sole or major product. Side products including isomeric alkenes 7 and 8, isomeric chlorides 9 and 10, isomeric triarylated isobutanes 11-14, 1-methyl-3-phenylindan (5) and 2-methyl-1-phenylindene (6) were also detected by GC-MS technique. Mechanistic interpretations and explanatory comments are offered.
Rhodium-catalyzed C-C coupling reactions involving ring opening of strained molecules. II. Addition to olefins and aromatic substitution
Chiusoli, Gian Paolo,Costa, Mirco,Melli, Luca
, p. 495 - 506 (2007/10/02)
Rhodium-catalyzed C-C coupling reactions, involving ring opening of strained molecules, have been studied using diphenylmethylenecyclopropanes as models.It has been established that, as rhodium takes control of the ring opening process, activated olefins
Ozonolysis of a Series of 1-Substituted Indenes. The Substituent Steric Effects on Ozonide Exo/Endo Ratios
Miura, Masahiro,Nojima, Masatomo,Kusabayashi, Shigekazu,McCullough, Kevin J.
, p. 2932 - 2936 (2007/10/02)
The ozonolysis of a series of disubstituted (1,2 and 1,3) and trisubstituted (1,2,3) indenes 1-28 in carbon tetrachloride at 20 deg C has been investigated.The major product in each case was the corresponding bicyclic ozonide, usually obtained as a mixtur
Sigmatropic Indenyl Rearrangements Induced by Electronic Excitation
Padwa, Albert,Goldstein, Steven,Loza, Roman,Pulwer, Mitchell
, p. 1858 - 1868 (2007/10/02)
The photochemical rearrangement of several arylalkyl substituted indenes has been studied.The rearrangements were shown to be derived from the ?,?* singlet state since triplet sensitization led to no reaction or else resulted in a Paterno-Buchi
