132-65-0Relevant articles and documents
First preparation and crystal structure of heterocyclic λ6-sulfanenitrile, 2,2′-biphenylylene(phenyl)-λ6-sulfanenitrile
Fujii, Takayoshi,Itoh, Akiko,Hamata, Kouki,Yoshimura, Toshiaki
, p. 5041 - 5043 (2001)
The first heterocyclic λ6-sulfanenitrile, 2,2′-biphenylylene(phenyl)-λ6-sulfanenitrile is prepared and its molecular and electronic structures are determined by X-ray crystallographic analysis and quantum chemical calculations, respectively.
EFFECT OF RING SIZE ON PHOTOREACTIVITY OF MEDIUM AND LARGE RING ESTERS.
Kulkarni, V. S.,Kulkarni, N. N.,Lele, S. R.,Hosangadi, B. D.
, p. 6169 - 6174 (1988)
Photochemical studies on 7,8,12,14,16 and 20 membered cyclic esters have been carried out in benzene and methanol.Decarboxylation and solvolysis ascribable to β- and α-scission respectively are observed in case of seven and eight membered cyclic esters.Larger rings do not undergo these photoreactions thus demonsrating effect of ring size on photoreactivity.
Reactivity of sulfur-containing molecules on noble metal surfaces. 4. Benzenethiol on Au(110)
Jaffey, Deborah M.,Madix, Robert J.
, p. 3020 - 3027 (1994)
The adsorption of benzenethiol on clean and sulfided Au(110) surfaces has been investigated with temperature programmed reaction spectroscopy. The monolayer is saturated at an benzenethiol coverage of 0.25 monolayers. About one-half of the thiol adsorbed at 100 K undergoes S-H bond cleavage below 300 K to form phenyl thiolate; H2 and H2S are evolved between 150 and 350 K. Phenyl thiolate decomposes above 400 K on clean Au(110) to yield mainly biphenyl, together with diphenyl sulfide, benzenethiol, and dibenzothiophene. With sulfidation of the Au(110) surface, the yield of biphenyl drops, while that of diphenyl sulfide rises. The range of products formed arises from competing C-S bond cleavage and C-H bond cleavage processes.
Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon-sulfur and carbon-hydrogen bonds
Tobisu, Mamoru,Masuya, Yoshihiro,Baba, Katsuaki,Chatani, Naoto
, p. 2587 - 2591 (2016)
A new process has been developed for the palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of C-H and C-S bonds. In contrast to the existing methods for the synthesis of this scaffold by C-H functionalization, this new catalytic C-H/C-S coupling method does not require the presence of an external stoichiometric oxidant or reactive functionalities such as C-X or S-H, allowing its application to the synthesis of elaborate π-systems. Notably, the product-forming step of this reaction lies in an oxidative addition step rather than a reductive elimination step, making this reaction mechanistically uncommon.
Polar Diels-Alder reactions using electrophilic nitrobenzothiophenes. A combined experimental and DFT study
Della Rosa, Claudia D.,Mancini, Pedro M.E.,Kneeteman, Maria N.,Lopez Baena, Anna F.,Suligoy, Melisa A.,Domingo, Luis R.
, p. 47 - 53 (2014)
The reactions between 2- and 3-nitrobenzothiophenes with three dienes of different nucleophilicity, 1-methoxy-3-trimethylsilyloxy-1,3-butadiene, 1-trimethylsilyloxy-1,3-butadiene and isoprene developed in anhydrous benzene and alternative under microwave irradiation with molecular solvents or in free solvent conditions, respectively, for produce dibenzothiophenes permit to conclude that both nitroheterocycles act as electrophile with the cited dienes. In the cases of the dienes 1-methoxy-3-trimethylsilyloxy-1,3-butadiene and 1-trimethylsilyloxy-1,3-butadiene which posses major nucleophilicity the observed product is the normal cycloaddition one. However when the diene is isoprene the product with both electrophiles follow the hetero Diels-Alder way. These reactions are considered polar cycloaddition reactions and the yields are reasonables. Moreover the polar Diels-Alder reactions of nitrobenzothiophenes with electron rich dienes 1-trimethylsilyloxy-1,3-butadiene have been theoretically studied using DFT methods.
Generation and detection of tellurane [10-Te-4(C4)] and selenurane [10-Se-4(C4)] having alkyl and aryl ligands
Sato, Soichi,Matsuo, Makoto,Nakahodo, Tsukasa,Furukawa, Naomichi,Nabeshima, Tatsuya
, p. 8091 - 8093 (2005)
Formation of 2,2′-biphenylylenedimethylselenurane and -tellurane was observed by the 1H, 13C, 77Se, and 125Te NMR studies at low temperature, in the reactions of dibenzoselenophene Se-oxide and 2,2′-biphenylylenedibromotellurane with methyllithium. These hypervalent compounds were unstable and decomposed at room temperature to give the corresponding dibenzochalcogenophenes quantitatively.
Aryl-aryl bond formation by flash vacuum pyrolysis of benzannulated thiopyrans
Amick, Aaron W.,Wakamiya, Atsushi,Scott, Lawrence T.
, p. 5119 - 5122 (2008)
(Chemical Equation Presented) In contrast to fully unsaturated 7-membered ring sulfur heterocycles (thiepines), some of which extrude sulfur and give the ring-contracted hydrocarbon even at room temperature in solution, benzannulated thiopyrans (6-membere
Synthesis of NiMo Catalysts Supported on Gallium-Containing Mesoporous y Zeolites with Different Gallium Contents and Their High Activities in the Hydrodesulfurization of 4,6-Dimethyldibenzothiophene
Zhou, Wenwu,Liu, Meifang,Zhang, Qing,Wei, Qiang,Ding, Sijia,Zhou, Yasong
, p. 7665 - 7679 (2017)
Mesoporous MY-xGa zeolites exhibiting both crystallized pore walls and narrowly dispersed mesopores with different Ga content were successfully synthesized. The synthesized samples were characterized by XRD, N2 adsorption desorption isotherms, SEM, TEM, XPS, FTIR, 29Si MAS NMR, 71Ga MAS NMR, and Py-FTIR methods. The results show that the synthesized samples exhibit unique open channel like mesopore systems and outstanding crystallite natures; no nonframework Ga species were observed over the MY-xGa series samples, and their acidic properties can be modulated by varying the Ga/Al ratio in the initial synthesis gel. The corresponding NiMo/HMY-xGa catalysts were prepared via the incipient wetness coimpregnation method; the morphologies of the sulfide catalysts were characterized by HRTEM, and the covalent states of the active metals were characterized by XPS. The catalytic activities of the investigated catalysts for the 4,6-DMDBT HDS reaction were assessed, and the collected products were analyzed by GC and GC-MS methods. The catalyst NiMo/HMY-0.5Ga showed the highest catalytic activity due to the synergistic effect of modulated acidic properties, excellent morphology, highest sulfidation degree, and proper proportion of NiMoS phase. More importantly, 4-MDBT, DBT, and BP were observed and identified as the products of the 4,6-DMDBT HDS reaction, designated as the demethylation pathway (DM) for the 4,6-DMDBT HDS reaction. Finally, a reaction network including DDS, HYD, ISO, and DM pathways for the 4,6-DMDBT HDS reaction over catalyst NiMo/HMY-0.5Ga was proposed.
Iron-catalyzed carbon–sulfur bond formation: Atom-economic construction of thioethers with diaryliodonium salts
Liu, Li,Qiang, Jian,Bai, Shuhua,Li, Yang,Li, Jian
, p. 2365 - 2371 (2017)
Diaryliodonium salts are characterized by poor atom economy with the formation of one equivalent of an iodoarene as waste. We have developed an atom-economic iron-catalyzed protocol for the synthesis of a variety of thioethers with diaryliodonium salts. Not only cyclic diaryliodonium salts but also linear diaryliodonium salts were found to perform well in the reactions.
Towards a general scale of nucleophilicity?
Phan, Thanh Binh,Breugst, Martin,Mayr, Herbert
, p. 3869 - 3874 (2006)
(Chemical Equation Presented) One for all? The nucleophilicity parameters N, which have been derived from the rate constants k of reactions of nucleophiles with carbocations, also hold for SN2-type reactions (see scheme). A general equation is suggested which includes established correlations (Swain-Scott, Ritchie) as special cases.
Transition-Metal-Free Diarylannulated Sulfide and Selenide Construction via Radical/Anion-Mediated Sulfur-Iodine and Selenium-Iodine Exchange
Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng
, p. 5756 - 5759 (2016)
A facile, straightforward protocol was established for diarylannulated sulfide and selenide construction through S-I and Se-I exchange without transition metal assistance. Elemental sulfur and selenium served as the chalcogen source. Diarylannulated sulfides were systematically achieved from a five- to eight-membered ring. A trisulfur radical anion was demonstrated as the initiator for this radical process via electron paramagnetic resonance (EPR) study. OFET molecules [1]benzothieno[3,2-b][1]benzothiophene (BTBT) and [1]benzothieno[3,2-b][1]benzoselenophene (BTBS) were efficiently established.
Synthesis and properties of thieno[2,3-d:5,4-d']bisthiazoles and their oxidized derivatives: Thionyl chloride as a sulfurative ring-fusing reagent towards thiophene-based ring-fused heteroaromatic compounds
Wada, Ryuta,Kaga, Shigesaki,Kawai, Yasuhiro,Futamura, Kimitaka,Murai, Toshiaki,Shibahara, Fumitoshi
, (2021/02/21)
A new route to thiophene-ring-fused compounds with thionyl chloride as a sulfur source was developed. Use of an excess amount thionyl chloride directly gave the corresponding thiophene-ring-fused compound via further reduction of generated thiophene-S-oxide with excess thionyl chloride in some cases. One-pot reduction with tributylphosphine also gave thiophene-ring-fused compounds in good yields, and oxidation with NaClO·5H2O gave S-dioxides. In addition, one of the obtained thiazole-thiophene ring-fused compounds showed some unexpected mechanochromism behavior.
α-Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1-(Dialkylamino)-1,2,3-triazoles
Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel
, p. 6943 - 6948 (2021/02/26)
The one-pot synthesis of a series of sulfonium salts containing transferable diazomethyl groups is described, and the structure of these compounds is elucidated by X-ray crystallography. Under photochemical conditions, reaction of these salts with N,N-dialkyl hydrazones affords 1-(dialkylamino)-1,2,3-triazoles via diazomethyl radical addition to the azomethine carbon followed by intramolecular ring closure. The straightforward transformation of the structures thus obtained into mesoionic carbene–metal complexes is also reported and the donor properties of these new ligands characterized.
A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
Huang, Binbin,Guo, Lin,Xia, Wujiong
supporting information, p. 2095 - 2103 (2021/03/26)
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
