58618-94-3Relevant academic research and scientific papers
One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions
Liao, Yen-Sen,Liang, Chien-Fu
supporting information, p. 1871 - 1881 (2018/03/23)
In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.
Oxidative self-coupling of aldehydes in the presence of CuCl2/TBHP system: Direct access to symmetrical anhydrides
Saberi, Dariush,Shojaeyan, Fatemeh,Niknam, Khodabakhsh
, p. 566 - 569 (2016/01/20)
A simple synthesis of symmetrical anhydrides has been developed. Using tert-butylhydroperoxide (TBHP) as the oxidant and copper(II) chloride as the catalyst in acetonitrile, various aromatic and heteroaromatic aldehydes were reacted to provide symmetrical anhydrides in modest to good yields.
COBALT(II) CHLORIDE CATALYZED SYNTHESES OF ACID ANHYDRIDES FROM ACID CHLORIDES
Srivastava, Rajiv R.,Kabalka, George W.
, p. 593 - 594 (2007/10/02)
Acid anhydrides were synthesized by reacting acid chlorides with carboxylic acids in the presence of catalytic quantities of cobalt(II) chloride.
One-electron Oxidation of Closed-shell Molecules. Part 4. Acid-induced Oxidative Cleavage of Substituted 1,2,2,2-Tetraphenylethanones (Benzpinacolones) with Diaroyl Peroxides
Kitagawa, Toshikazu,Takeuchi, Ken'ichi,Murai, Osamu,Matsui, Shin,Inoue, Takeshi,Nishimura, Makoto et al.
, p. 1987 - 1996 (2007/10/02)
The acid-induced oxidative cleavage of anispinacolone with diaroyl peroxides in 1,2-dichloroethane-trifluoroacetic acid (TFA) has been investigated.The principal two products after work-up are tris-(p-methoxyphenyl)methanol and p-methoxybenzoic acid; the latter was found as anhydrides in the reaction mixture.Free-radical formation in the course of the cleavage was verified by polymerization of added acrylonitrile in the oxidation by bis-(3,5-dinitrobenzoyl) peroxide.When the oxidation of anispinacolone (90percent (13)C) by dibenzoyl peroxide was carried out in a (13)C n.m.r. probe, an emission peak, assigned to p-methoxybenzoic trifluoroacetic anhydride, was observed.The logarithms of the rate constants for oxidation of p-substituted benzpinacolones by dibenzoyl peroxide were linearly correlated with the oxidation potentials of the benzpinacolones.These results are consistent with a single-electron transfer (s.e.t.) pathway from benzpinacolones to dibenzoyl peroxide.The oxidation is first-order in each reactant and is promoted by TFA.The effect of TFA is accounted for by two factors, (i) assisted O-O bond cleavage of the peroxide radical anion by TFA, and (ii) the formation of protonated peroxide, a more powerful oxidizing species.The former factor is dominant at lower TFA concentrations ( 0.05 M), the latter at higher concentrations.
PHASE MANAGED ORGANIC SYNTHESIS 2. A NEW POLYMER ASSISTED SYNTHESIS OF ACID ANHYDRIDES.
Fife, Wilmer K.,Zhang, Zhi-dong
, p. 4933 - 4936 (2007/10/02)
A solid-phase copolymer of 4-vinylpyridine is shown to be a highly effective reagent/catalyst for the synthesis of acid anhydrides from mixtures containing equimolar quantities of carboxylic acid and acid chlorides.The process may be carried out in batch or column mode.
One-electron Oxidation of Closed-shell Molecules. Part 3. Oxidative Cleavage of 1,2,2,2-Tetrakis-(p-methoxyphenyl)ethanone with Dibenzoyl and Bis(3,5-dinitrobenzoyl) Peroxides: Mechanistic Changeover of the Peroxide Function from Radical to Molecular Oxidation
Takeuchi, Ken'ichi,Murai, Osamu,Matsui, Shin,Inoue, Takeshi,Kitagawa, Toshikazu,Okamoto, Kunio
, p. 1301 - 1310 (2007/10/02)
1,2,2,2-Tetrakis-(p-methoxyphenyl)ethanone (anispinacolone) (1) is cleaved by dibenzoyl peroxide (2) or bis-(3,5-dinitrobenzoyl) peroxide (3), affording tris-(p-methoxyphenyl)methyl benzoate (or 3,5-dinitrobenzoate) and benzoic (or 3,5-dinitrobenzoic) p-methoxybenzoic anhydride as the principal cleavage products. 13C N.m.r.CIDNP studies by use of labelled anispinacolone (An3*C-*COAn ; *C 90percent 13C) indicated that p-methoxybenzoyl radical is formed, presumably by way of the radical cation +. which is produced by a single-electron transfer (s.e.t.) mechanism.The formation of the p-methoxybenzoyl radical was also indicated by spin-trapping experiments.The decomposition rates of (2) at 50.0 deg C are unaltered on addition of (1) in nonpolar solvents such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and benzene, whereas those of (3) are markedly accelerated.The cleavage of (1) by (2) is supressed by added 3,4-dichlorostyrene by a factor of 6.7, whereas that of (1) by (3) is almost unaffected.These results suggest that in the case of dibenzoyl peroxide (2) the thermally produced benzoyloxyl radical works as a one-electron acceptor (or oxidant) upon (1), whereas when bis-(3,5-dinitrobenzoyl) peroxide (3) is used the peroxide molecule oxidizes (1), probably by way of an s.e.t. mechanism even in such nonpolar solvents.On the other hand, in polar solvents such as (CF3)2CHOH, teramethylene sulphone, and acetonitrile the decomposition of (2) is accelerated by added anispinacolone, suggesting that the intermolecular s.e.t. reaction is partially involved in such polar solvents.Consequently, the oxidative cleavage of anispinacolone (1) by diaroyl peroxides provides the first example of dichotomy in the s.e.t. reaction of diaroyl peroxides, which can be considered a counterpart of the SN1-SN2 dichotomy in nucleophilic substitution, as far as the molecularity of the peroxide is concerned.
