58808-66-5Relevant academic research and scientific papers
Alkyl-and arylsulfanyl-substituted unsaturated carbonyl compounds
Kondrashov, Evgeniy V.,Romanov, Alexey R.,Ushakov, Igor A.,Rulev, Alexander Yu.
, p. 18 - 33 (2017/01/17)
A method for the synthesis of captodative sulfanyl enals, enones and enoates via nucleophilic vinylic substitution of corresponding halogen-bearing derivatives has been developed. The one-pot treatment of the haloenoates, haloenones or haloenals with thiols in the presence of organic base leads either to vicinal dithiosubstituted carbonyl-bearing compound or captodative systems with good to excellent yield. The major reaction direction strongly depends on the type of base used.
A recyclable biphasic system for stereoselective and easily handled hydrochalcogenations
Tidei, Caterina,Sancineto, Luca,Bagnoli, Luana,Battistelli, Benedetta,Marini, Francesca,Santi, Claudio
supporting information, p. 5968 - 5975 (2015/03/30)
Vinyl selenides and vinyl sulfides were prepared by hydrochalcogenation of alkynes with selenols and thiols generated in situ by the reduction of the corresponding diselenides and disulfides with elemental zinc in a biphasic acidic medium. The yields, ste
Preparation and chemistry of phosphoranyl-derived iodanes
Zhdankin, Viktor V.,Maydanovych, Olena,Herschbach, Jon,Bruno, Jessica,Matveeva, Elena D.,Zefirov, Nikolai S.
, p. 1018 - 1023 (2007/10/03)
The preparation and chemistry of novel phosphoranyl-derived λ3-iodanes is reported. The phosphoranyl-derived phenyliodonium sulfonates were prepared in good yields by the reaction of stabilized phosphonium ylides [1-triphenylphosphoranylidene-2-propanone, methyl(triphenylphosphoranylidene)acetate, (triphenylphosphoranylidene)acetaldehyde, and (triphenylphosphoranylidene)acetonitrile] with the pyridinium complex of iodobenzene ditriflate or with [hydroxy(tosyloxy)-iodo]benzene under mild conditions. These compounds represent a potentially useful class of reagents that combine in one molecule synthetic advantages of a phosphonium ylide and an iodonium salt. Specifically, phosphorane-derived phenyliodonium tosylates can react with soft nucleophiles, such as iodide, bromide, benzenesulfinate, and thiophenolate anions, with a selective formation of the respective α-functionalized phosphonium ylides, which can be further converted to alkenes by the Wittig reaction with benzaldehyde. The phosphoranyl-derived benziodoxoles can be prepared by the reaction of 1-acetoxybenziodoxole with stabilized phosphonium ylides. An unusual ligand exchange on the iodine(III) center resulting in the substitution of a carbon ligand with an oxygen ligand was observed in the reaction of these compounds with strong acids.
ADDITION OF THIOLS TO DERIVATIVES OF PHENYLPROPYNOIC ACID
Rasteikene, L. P.,Vidugirene, V. I.,Talaikite, Z. A.,Lukoshyavichyute, N. M.
, p. 647 - 651 (2007/10/02)
The reaction of thiophenol and benzyl hydrosulfide with phenylpropynoic acid, its methyl ester, and its anilide was investigated.The addition of thiophenol takes place regioselectively.Under the conditions of a radical reaction derivatives of 2-phenylthio
Reaction of Benzenesulphenyl Chloride with α, β-Unsaturated Compounds: Part I - Reactions with Methyl Crotonate and Methyl Cinnamate in Presence of Pyridine
Bhongle, N. N.,Gogte, V. N.,Vankar, Y. D.
, p. 724 - 728 (2007/10/02)
Reaction of benzenesulphenyl chloride (PhSCl) with α, β-unsaturated systems, in the presence of pyridine, offers a convenient route to sulphenylate regiospecifically the α-position of such systems.The specific role of pyridine and the product analysis have been examined and rationalised on the basis of the formation of pyridine-assisted carbanion intermediates and the structure/stability of these carbanions.
THE AdNSNE MECHANISM IN THE REACTION OF PHENOL AND BENZENETHIOL WITH α-BROMO MICHAEL ACCEPTORS IN THE K2CO3-ACETONE SYSTEM
Rosnati, Vittorio,Saba, Antonio,Salimbeni, Aldo,Vettori, Umberto
, p. 249 - 256 (2007/10/02)
In the reaction of α-bromo Michael acceptors with either phenol or benzenethiol formal substitution of the vinylic bromine proceeds through addition of the phenolic reagent, followed by nucleophilic substitution and β-elimination (AdNSNE mechanism) in the system K2CO3-acetone.The process is shown to be stereospecific in the case of 2a,b and 3b,c, leading to the corresponding Z isomer.The reactivity of substrates 1-4 is discussed in terms of their structural features.
Preparation of β-Hydroxy-α-phenylthio Esters via Condensation of Aldehydes with α-Phenylthio Ester Enolate Anions
Hoye, Thomas R.,Kurth, Mark J.
, p. 3549 - 3554 (2007/10/02)
The lithium enolates of α-phenylthio esters 5 react with aldehydes 6 to give good yields of diastereomeric aldol products 7 and 8 provided that anhydrous zinc chloride is first added to the enolate solution.The threo or erythro nature of several of the al
