110143-20-9Relevant academic research and scientific papers
Effective α-tosyloxylation of ketones using 1,1,1-trifluoro-2-iodoethane as catalyst
Zhang, Bijun,Han, Liuquan,Hu, Jiantao,Yan, Jie
, p. 3264 - 3270 (2014)
With 1,1,1-trifluoro-2-iodoethane as catalyst, a novel and efficient procedure has been developed for preparation of α-tosyloxyketones from ketones. In this protocol, 1,1,1-trifluoro-2-iodoethane is first oxidized by m-chloroperbenzoic acid to a hypervale
4-MeC6H4I-mediated efficient -tosyloxylation of ketones with oxone and p- toluenesulfonic acid in acetonitrile
Tanaka, Ayumi,Togo, Hideo
, p. 3360 - 3364 (2009)
Various alkyl aryl ketones, dialkyl ketones, and cycloheptanone were efficiently converted into the corresponding -tosyl-oxy ketones in good yields by using Oxone and p-toluenesulfonic acid monohydrate in the presence of p-iodotoluene in aceton
Novel α-tosyloxylation of ketones catalyzed by the in situ generated hypoiodous acid from alkyl iodide
Zhang, Bijun,Han, Liuquan,Hu, Jiantao,Yan, Jie
, p. 5851 - 5854 (2015/01/16)
Using a catalytic amount of 1-iodopropane, a novel and efficient procedure has been developed for direct preparation of α-tosyloxyketones from ketones. In this protocol, 1-iodopropane is first oxidized into iodosylpropane, which decomposes to form the key
PhI- and polymer-supported PhI-catalyzed oxidative conversion of ketones and alcohols to α-tosyloxyketones with m-chloroperbenzoic acid and p-toluenesulfonic acid
Yamamoto, Yukiharu,Kawano, Yuhta,Toy, Patrick H.,Togo, Hideo
, p. 4680 - 4687 (2007/10/03)
Various ketones were converted to the corresponding α-tosyloxyketones with mCPBA and p-toluenesulfonic acid in the presence of a catalytic amount of iodobenzene. Moreover, secondary alcohols were directly converted to the corresponding α-tosyloxyketones using mCPBA and catalytic amounts of iodobenzene and potassium bromide, followed by treatment with p-toluenesulfonic acid in a one-pot manner. Poly(4-iodostyrene) could be also used as a recyclable catalyst for the same α-tosyloxylation of ketone.
Nucleophilic Substitution Reactions of Phenacyl Benzenesulphonates with Anilines in Methanol-Acetonitrile Mixtures
Lee, Ikchoon,Shim, Chang Sub,Chung, Soo Young,Lee, Hai Whang
, p. 975 - 982 (2007/10/02)
The nucleophilic substitution reactions of phenacyl benzenesulphonates with anilines in methanol-acetonitrile have been studied.A stronger nucleophile was found to cause less bond cleavage, while a better leaving group led to less bond formation, in compl
Enolate Structures Contributing to the Transition State for Nucleophilic Substitution on α-Substituted Carbonyl Compounds
Yousaf, T. I.,Lewis, E. S.
, p. 6137 - 6142 (2007/10/02)
The high SN2 reactivity of α-halocarbonyl compounds is explained by the lowering of the intrinsic barrier by a major contribution of enolate structure to the transition state.This theoretical conclusion is now shown experimentally.The evidence is as follows: (1) Change in structure of a leaving arenesulfonate ion does not change the rates of attack of benzenesulfonate ion by nearly as much as it changes the equilibrium constants.A charge on the transferring phenacyl group of -0.48 is deduced. (2) The ρ value (-3.9) for attack of substituted thiophenoxides on phenacyl bromide is much more negative than that for attack on methyl iodide (-1.8). (3) A related ρ value is found for reaction of 2,4,6-trimethylphenacyl bromide with thiophenoxides (-2.2), showing a lesser, but still large sensitivity to nucleophile structure where addition to the carbonyl is sterically forbidden.The enolate structure leaves the attacking or leaving nucleophiles with a single electron each instead of the unshared pairs.Thus, the enolate structure is emphesized if the leaving group and the nucleophile readily lose an electron.
