29555-29-1Relevant academic research and scientific papers
Tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds
Zhang, Zhen,Li, Cheng,Wang, Shao-Hua,Zhang, Fu-Min,Han, Xue,Tu, Yong-Qiang,Zhang, Xiao-Ming
, p. 3239 - 3247 (2017)
A novel and efficient tandem SN2′ nucleophilic substitution/oxidative radical cyclization reaction of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds has been developed by using Mn(OAc)3 as an oxidant, which enables t
Manganese(III)-based intramolecular macrocyclization of 3,3-diphenyl-2-propenyloxyoligomethylene 3-oxobutanoates
Jogo, Shunsuke,Nishino, Hiroshi,Yasutake, Mikio,Shinmyozu, Teruo
, p. 9031 - 9034 (2002)
The reaction of 3,3-diphenyl-2-propenyloxytetramethylene 3-oxobutanoate (14) with manganese(III) acetate dihydrate in boiling acetic acid caused the oxidative intramolecular radical cyclization to produce 13-methyl-11,11-diphenyl-3,8,12-trioxabicyclo[8.3.0]tridec-13-en-2-one (24) in 94% yield. A similar oxidation of the 3,3-diphenyl-2-propenyloxyoligomethylene 3-oxobutanoates (1n: n=2, 3, 6, 8) gave the corresponding macrolides 2n (n=2, 3, 6, 8) in moderate to good yields. A 17-membered crown ether-type macrolide 211 was also obtained in 80% yield by the intramolacular radical cyclization of the oxaethylene-tethered 3-oxobutanoate (111). The structure of the macrolides 2n (n=2, 3, 4, 6, 11) has been corroborated by an X-ray crystal structure analysis.
Pyridine ligands as promoters in PdII/0-catalyzed C-H olefination reactions
Kubota, Asako,Emmert, Marion H.,Sanford, Melanie S.
supporting information; experimental part, p. 1760 - 1763 (2012/05/20)
Commercially available pyridine ligands can significantly enhance the rate, yield, substrate scope, and site selectivity of arene C-H olefination (Fujiwara-Moritani) reactions. The use of a 1:1 ratio of Pd/pyridine proved critical to maximize reaction rates and yields.
Ligand-free Pd-catalyzed highly selective arylation of allylic esters with retention of the traditional leaving group
Pan, Delin,Chen, Anjun,Su, Yijin,Zhou, Wang,Li, Si,Jia, Wei,Xiao, Juan,Liu, Qingjian,Zhang, Liangren,Jiao, Ning
supporting information; experimental part, p. 4729 - 4732 (2009/02/06)
(Chemical Equation Presented) What leaving group? Organic halides and allylic esters undergo efficient Pd-catalyzed Heck reactions under mild conditions in air to form a new C-C bond without elimination of the β-OAc group in the intermediate palladium complex. Instead a highly regioselective β-H elimination takes place to provide substituted derivatives of allylic alcohols (see scheme).
[(NHC)Au1]-catalyzed rearrangement of allylic acetates
Marion, Nicolas,Gealageas, Ronan,Nolan, Steven P.
, p. 2653 - 2656 (2008/02/09)
Equation Presented [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.
Palladium catalyzed cyclocarbonylation of 3,3-diarylallyl acetates
Iwasaki, Masakazu,Ishii, Youichi,Hidai, Masanobu
, p. 435 - 442 (2007/10/02)
Palladium-catalyzed cyclocarbonylation of 3,3-diarylallyl acetates afforded 4-aryl-substituted 1-naphthyl acetates where the cyclization occurred selectively on the more electron-rich ring.
Oxidation by Cobalt(III) Acetate. Part 8. Effects of Substituents on Product Distributions in Oxidation of Aromatic Olefins by Cobalt(III) Acetate
Morimoto, Takashi,Hirano, Masao,Koyama, Tsuyoshi
, p. 1109 - 1116 (2007/10/02)
Oxidation of aromatic olefins by cobalt(III) acetate in acetic acid under nitrogen gave both allylic acetates and glycol monoacetates.Disubstituted olefins were oxidized by the oxidant to give predominantly allylic acetates.Glycol monoacetates were minor products except for the case of 1-phenylisobutene which was slowly oxidized to give the corresponding glycol monoacetate.In the oxidation of tri- and tetra-substituted olefins, the yield of glycol monoacetate increased at the expense of that of allylic acetate.A mechanism, in which the reaction proceeds through a Co-co-ordinated radical kation formed by an one-electron abstraction from olefin by cobalt(III) acetate, is suggested.
The Oxidation of 3,3-Diphenyl-2-propenoic Acid with Manganese(III) Acetate
Kurosawa, Kazu,Tsujita, Tsuyoshi
, p. 2391 - 2394 (2007/10/02)
The oxidation of 3,3-diphenyl-2-propenoic acid with manganese(III) acetate in boiling acetic gave 3,3-diphenyl-2-propenyl acetate, 4-acetoxymethyl-5,5-diphenyltetrahydro-2-furanone, 3,3-diphenyl-2-propenal, 5,5-diphenyl-2,5-dihydro-2-furanone, 4-acetoxy-5,5-diphenyltetrahydro-2-furanone, benzophenone, and 2-oxo-5,5-diphenyltetrahydro-4-furancarboxylic acid.The reaction pathways are discussed.
