42349-44-0Relevant academic research and scientific papers
Rhodium-Catalyzed Oxidative Decarboxylation Annulation Reactions of Mandelic Acids and Alkynes: An Efficient Synthetic Method for Indenones
Yu, Xiaobo,Duan, Yulian,Guo, Weijie,Wang, Tao,Xie, Qingxiao,Wu, Shutao,Jiang, Chenggong,Fan, Zixiong,Wang, Jianhui,Liu, Guiyan
, p. 1027 - 1034 (2017/04/21)
Efficient rhodium-catalyzed oxidative decarboxylation annulation reactions between mandelic acids and alkyne derivatives are described. The desired indenone products were obtained in medium to good yields under the optimized reaction conditions, which were a [RhCp*Cl2]2 catalyst (10.0 mol %) in combination with a PCy3 ligand (10.0 mol %) and AgSbF6 (10 mol %) and Cu(OAc)2 (20 mol %) additives. Many functional groups are compatible with the reaction under the optimized reaction conditions. This strategy provides a promising method for the construction of indenones from cheap and commercially available starting materials.
Sigmatropic Rearrangements of 1,1-Diarylindenes. Migratory Aptitudes of Aryl Migration in the Ground and Electronically Excited States
Manning, Carl,McClory, Michael R.,McCullough, John J.
, p. 919 - 930 (2007/10/02)
The photochemical and thermal rearrangements of 1,1-diarylindenes to give 2,3-diarylindenes have been investigated.Migratory aptitudes of p-X-phenyl vs. phenyl were determined for X =Br,CN, and OCH3 in the photochemical and thermal migrations.The identities of the products of these rearrangements were established by unambiguous synthesis, and the synthetic work is described.Product ratios were generally determined by NMR techniques, but VPC and isotope dilution were also used in the case of 1-(p-cyanophenyl)-1-phenylindene reactions.The excited-state reactions (direct and triplet sensitized) are highly selective, migration of the substituted phenyl group being favored for all three substituents.The thermal reactions, in contrast, are quite unselective, phenyl migrating almost as readily as the substituted phenyl group in all cases.Quantum yields for the rearrangement in the case of 1,1-diphenylindene and 1-(p-cyanophenyl)-1-phenylindene were 0.80 and 0.4, respectively (direct irradiation), and 0.43 and 0.53 (sensitized reactions).The results of the thermal reactions and results from the literature are discussed in terms of bond-dissociation energies and transition-state-delocalization energies calculated by using the Hueckel theory.Neither approach led to a satisfactory interpretation.The excited-state migrations are consistent with charge-transfer stabilization of the transition state, which can be estimated from oxidation and reduction potentials by using Weller's equation.
