4024-14-0Relevant articles and documents
Aromatic substituent effect on the stereoselectivity of the condensed- and gas-Phase Acid-Induced methanolysis in 2-Aryloxiranes derived from 3,4-dihydronaphthalene and trans-1,2,3,4,4a,10a-Hexahydrophenanthrene bearing a tertiary benzylic oxirane nucleophilic centre
Crotti, Paolo,Di Bussolo, Valeria,Favero, Lucilla,Pineschi, Mauro,Sergiampietri, Daniela,Renzi, Gabriele,Ricciutelli, Massimo,Roselli, Graziella
, p. 5515 - 5536 (1997)
The ring-opening reactions with MeOH of the title benzocondensed 2-aryl oxiranes 6 and 7a,b both in the condensed (methanolysis) and in the gas phase were examined, obtaining in all cases a good Hammett-type linear correlation. Results indicate that the secondary or tertiary nature of the benzylic oxirane carbon is not responsible for the different stereochemical behavior so far encountered in different 2-aryl oxirane systems under the same operating conditions.
Anodic oxidation triggered divergent 1,2- And 1,4-group transfer reactions of β-hydroxycarboxylic acids enabled by electrochemical regulation
Jiang, Yangye,Lu, Gang,Mo, Fanyang,Yang, Jianxin,Yang, Yang,Yin, Yunxing,Zeng, Chengchu,Zhang, Lei,Zhang, Xianhao,Zhang, Zhenxing
, p. 12021 - 12028 (2020/11/26)
We report a set of electrochemically regulated protocols for the divergent synthesis of ketones and β-keto esters from the same β-hydroxycarboxylic acid starting materials. Enabled by electrochemical control, the anodic oxidation of carboxylic acids proceeded in either a one-electron or a two-electron pathway, leading to a 1,4-aryl transfer or a semipinacol-type 1,2-group transfer product with excellent chemoselectivity. The 1,4-aryl transfer represents an unprecedented example of carbon-to-oxygen group transfer proceeding via a radical mechanism. In contrast to previously reported radical group transfer reactions, this 1,4-group transfer process features the migration of electron-rich aryl substituents. Furthermore, with these chemoselective electrochemical oxidation protocols, a range of ketones and β-keto esters including those possessing a challenging-to-access medium-sized ring could be synthesized in excellent yields. This journal is
Anti-Markovnikov Oxidation of β-Alkyl Styrenes with H2O as the Terminal Oxidant
Zhang, Guoting,Hu, Xia,Chiang, Chien-Wei,Yi, Hong,Pei, Pengkun,Singh, Atul K.,Lei, Aiwen
supporting information, p. 12037 - 12040 (2016/09/28)
Oxygenation of alkenes is one of the most straightforward routes for the construction of carbonyl compounds. Wacker oxidation provides a broadly useful strategy to convert the mineral oil into higher value-added carbonyl chemicals. However, the conventional Wacker chemistry remains problematic, such as the poor activity for internal alkenes, the lack of anti-Markovnikov regioselectivity, and the high cost and chemical waste resulted from noble metal catalysts and stoichiometric oxidant. Here, we describe an unprecedented dehydrogenative oxygenation of β-alkyl styrenes and their derivatives with water under external-oxidant-free conditions by utilizing the synergistic effect of photocatalysis and proton-reduction catalysis that can address these challenges. This dual catalytic system possesses the single anti-Markovnikov selectivity due to the property of the visible-light-induced alkene radical cation intermediate.
Synthesis of 2-tetralone derivatives by Bi(OTf)3-catalyzed intramolecular hydroarylation/isomerization of propargyl alcohols
Yun, Jihee,Park, Jungmin,Kim, Jaehyun,Lee, Kooyeon
, p. 1045 - 1048 (2015/02/19)
Compared to 1-tetralones, 2-tetralones are expensive, less stable, and difficult to synthesize. A concise Bi-catalyzed method was developed for the synthesis of 2-tetralones from 5-phenylpent-1-yn-3-ol derivatives. Diverse 2-tetralones were obtained in moderate to good yields under mild conditions.
