113160-01-3Relevant academic research and scientific papers
The photochemical addition of 2,2,2-trifluoroethanol to methoxy-substituted stilbenes
Roberts, Jeffrey C.,Pincock, James A.
, p. 4279 - 4282 (2004)
The excited-state lifetime of the trans-stilbene chromophore in acetonitrile is prolonged by methoxy substituents in the meta positions. The long-lived singlet excited state of trans-3,5-dimethoxystilbene (trans-2d) is quenched upon the addition of 2,2,2-trifluoroethanol (TFE), and the Markovnikov ether is observed as the major product from steady-state irradiations. The results indicate that the reaction pathway proceeds through a carbocation intermediate.
Transition-Metal-Free Catalytic Carboalkoxylation of Styrenes at Room Temperature
Govindarajan,Ahmed, Jasimuddin,Swain, Asim Kumar,Mandal, Swadhin K.
supporting information, p. 13490 - 13502 (2019/10/16)
Herein, we describe the first transition-metal-free catalytic carboalkoxylation of styrenes with aryl diazonium salts by Meerwein addition in the presence of a phenalenyl ligand at room temperature without requiring any light stimulation. This three-compo
Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions
Jereb, Marjan,Vra?i?, Dejan
, p. 747 - 762 (2018/01/17)
Iodine-catalyzed transformations of alcohols under solvent-free reaction conditions (SFRC) and under highly concentrated reaction conditions (HCRC) in the presence of various solvents were studied in order to gain insight into the behavior of the reaction intermediates under these conditions. Dimerization, dehydration and substitution were the three types of transformations observed with benzylic alcohols. Dimerization and substitution reactions were predominant in the case of primary- and secondary alcohols, whereas dehydration prevailed in the case of tertiary alcohols. The relative reactivity of substituted 1-phenylethanols in I2-catalyzed dimerization under SFRC provided a good Hammett plot ρ+ = -2.8 (r2 = 0.98), suggesting the presence of electron-deficient intermediates with a certain degree of developed charge in the rate-determining step.
Oxyarylation and aminoarylation of styrenes using photoredox catalysis
Fumagalli, Gabriele,Boyd, Scott,Greaney, Michael F.
supporting information, p. 4398 - 4401 (2013/09/24)
A three-component coupling of styrenes is reported, using photoredox catalysis to achieve simultaneous arylation and C-O or C-N bond formation across the styrene double bond.
Photochemical Addition of Methanol to Stilbenes
Woning, Jan,Oudenampsen, Albert,Laarhoven, Wim H.
, p. 2147 - 2154 (2007/10/02)
The photochemical addition of methanol to the alkenic bond of stilbene (1) involves two competitive pathways: viz. either direct addition of methanol to the alkenic bond or insertion by methanol of a carbene (13), emerging from a 1,2-H shift in (1).From the observed effect of substituents and the wavelength on the rates of these processes, the rearrangement pathway was concluded to involve excited (1) in a vibrationally unrelaxed S1-state.The direct pathway might involve either a planar (??*) or a twisted excited S1-state of (1).The available experimental evidence precludes zwitterionic excited states from being involved in both pathways.The photochemical addition of methanol to the alkenic bond of 1,1-diphenylethene (3) follows a similar course.In this case a 1,2-Ph shift in excited (3) gives rise to carbene (13) and its insertion products.
Ceric Ammonium Nitrate Oxidative-Cleavage Reaction of Some Lignin Model Compounds: Role of the Benzylic Hydroxyl Group
Fisher, Thomas H.,Dershem, Stephen M.,Schultz, Tor P.
, p. 1504 - 1507 (2007/10/02)
A series of β-1 lignin model compounds was synthesized and then oxidized with ceric ammonium nitrate (CAN) in aqueous acetonitrile.The compounds studied were 1,2-diarylethanols with either a p-hydroxy (1a-e) or a p-methoxy (2a-e) on the 1-ring and the following para substituents on the 2-ring: (a) H, (b) Cl, (c) Me, (d) OMe, and (e) NO2.Reactions of p-hydroxyl compounds 1a-e with CAN resulted in the formation of a red cerium complex that did not oxidize under the conditions of the reaction.In contrast all of the methoxy compounds 2a-e were rapidly oxidized by CAN atroom temperature to give p-anisaldehyde in near quatitative yield.The relative rates of these oxidative-cleavage reactions were found to be 0.11, 0.16, 1.00, 1.58, and 2.37 for the 1,2-diarylethanols 2e, 2b, 2a, 2c, and 2d, respectively.A Hammett treatment of this data revealed an excellent correlation with ?(ρ = -1.24).Methylation of the benzylic hydroxy group of 2a gave 1-methoxy-1-(4-methoxyphenyl)-2-phenylethane, which was found to be inert to CAN oxidation.
