882-33-7Relevant articles and documents
Cycloaddition Reactions of Highly Stabilized Isoquinolinium Methylides to Nonactivated Olefins and Electron-Rich Olefins
Tsuge, Otohiko,Kanemasa, Shuji,Sakamoto, Kazushige,Takenaka, Shigeori
, p. 2513 - 2524 (1988)
Highly stabilized isoquinolinium methylides bearing two electron-withdrawing substituents at the ylide carbon undergo cycloadditions with aryl-substituted olefins (acenaphthylene,(E)- and (Z)-stilbenes, indene, and stirene), alkyl-substituted olefins (norbornene, (Z)-3-hexene-1,6-dinitrile, 1-hexene, 2-propen-1-ol, and 3-(trimethylsilyloxy)propene), and electron-rich olefins (vinylene carbonate, butyl vinyl ether, and phenyl vinyl sulfide).These cycloadditions proceed in an exclusively regioselective and mostly stereoselective manner.
Reactions of arenediazonium salts with diazadithiafulvalenes
Koizumi, Toshio,Bashir, Nadeem,Murphy, John A.
, p. 7635 - 7638 (1997)
The kinetics of coupling of carbon radicals with sulfur radical-cations in diazadithiafulvalenes is sensitive to the steric environment around sulfur.
Structure-activity relationships of phenyl- and benzoylpyrroles
Laatsch,Renneberg,Hanefeld,Kellner,Pudleiner,Hamprecht,Kraemer,Anke
, p. 537 - 546 (1995)
Antitumor, antimicrobial, and phytotoxic activities of the marine antibiotic pentabromopseudilin (la) and related phenyl-, benzyl- and benzoyl pyrroles were compared. All activities depended strongly on the substituent pattern, with the natural compound 1a being the most active one. As judged from model reactions, a covalent bond of nucleophiles to the pyrrole system may be involved in the inhibition of macromolecular syntheses.
Electrogeneration of triphenyltin radical, anion, and cation. Electrochemical initiation of tin hydride-promoted radical chain reactions
Tanaka, Hideo,Ogawa, Hidenori,Suga, Hiroaki,Torii, Sigeru,Jutand, Anny,Aziz, Said,Suarez, Alejandra G.,Amatore, Christian
, p. 9402 - 9408 (1996)
In our research of precursors of tin radicals able to initiate radical chain reactions under mild conditions, a series of triphenyltin derivatives Ph3SnY (Y = H, I, Cl, OTf, OCHO, SnPh3, SPh) is investigated by cyclic voltammetry. The results show that the tin radical Ph3Sn. is only produced from two compounds: by a one-electron oxidation of Ph3SnH or by a one-electron reduction of Ph3-SnI. Therefore electrooxidation of Ph3SnH generates Ph3Sn. which is able to initiate cyclization of haloalkynes. Reduction or oxidation of the other derivatives affords respectively the anion Ph3Sn- or the cation Ph3Sn+ because they are generated at potentials where the radical Ph3Sn. is either reduced or oxidized.
Metal- and solvent-free, iodine-catalyzed cyclocondensation and C[sbnd]H bond sulphenylation: A facile access to C-4 sulfenylated pyrazoles via a domino multicomponent reaction
Sun, Pengfei,Yang, Daoshan,Wei, Wei,Sun, Xuejun,Zhang, Wenhui,Zhang, Hui,Wang, Yu,Wang, Hua
, p. 2022 - 2029 (2017)
We describe herein a green and efficient MCRs protocol to synthesize C-4 sulfenylated pyrazoles by iodine-catalyzed cyclocondensation and direct C[sbnd]H bond sulphenylation reactions. Through this protocol, two new C[sbnd]N bonds and one C[sbnd]S bond ar
Visible-light-mediated defluorinative cross-coupling of: Gem-difluoroalkenes with thiols
Wang, Junlei,Huang, Binbin,Yang, Chao,Xia, Wujiong
, p. 11103 - 11106 (2019)
Here we report a visible-light-mediated monofluoroalkenylation through defluorinative cross-coupling of gem-difluoroalkenes with aryl, benzyl, and alkyl thiols. This novel strategy provides facile and efficient access to tri/tetra-substituted monofluoroalkenes under mild reaction conditions with good functional group tolerance. Late-stage modification of natural products indicated the synthetic potential of this S-H monofluoroalkenylation process.
Stereoselective access to trisubstituted fluorinated alkenyl thioethers
Fabre, Indira,Poisson, Thomas,Pannecoucke, Xavier,Gillaizeau, Isabelle,Ciofini, Ilaria,Grimaud, Laurence
, p. 1921 - 1927 (2017)
We report the first copper-catalyzed olefinic ethoxy carbonyl difluoromethylation of alkenyl thioethers via direct C-H bond functionalization using BrCF2COOEt. The developed methodology allows the preparation of trisubstituted olefins with a controlled stereochemistry. A mechanistic study is reported and a radical mechanism is revealed.
Rhodium-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Sulfur Nucleophiles
Leong, Paul,Lautens, Mark
, p. 2194 - 2196 (2004)
The synthesis of 2-sulfanyl-1,2-dihydro-naphthalen-1-ols is described. This methodology is based on rhodium catalysis and enables various thiols to undergo an asymmetric SN2′ ring opening of oxabenzonorbornadiene. Under the reaction conditions
Mixed-chalcogenide diplatinum complexes; an investigation of ligand exchange processes using ESI mass spectrometry
Fortney-Zirker, Ryland G.,Henderson, William,Tiekink, Edward R.T.
, p. 83 - 96 (2017)
Routes to mixed-chalcogen diplatinum complexes have been explored using Electrospray Ionisation Mass Spectrometry (ESI-MS) as a powerful technique to probe reaction solutions on the microscale. Exchange reactions of binuclear platinum(II) complexes [Ptsu
Cryoelectrochemical reduction of a phenyl sulfide in tetrahydrofuran: Mediated reduction gives different products compared to direct reduction
Burasov, Alexander V.,Paddon, Christopher A.,Bhatti, Earrah L.,Donohoe, Timothy J.,Compton, Richard G.
, p. 144 - 150 (2007)
An electrocatalytic reduction of [(3-{[trans-4-(methoxymethoxy)cyclohexyl] oxy}propyl)thio]benzene (RSPh) in the presence of naphthalene as a mediator is investigated, using steady-state voltammetry at various sized platinum microelectrodes and at low temperature (201 K) in tetrahydrofuran (THF). This mediated process has been found to involve the transfer of one electron, in contrast to the direct electrochemical reduction which involves two electrons. In addition, the mediated reduction proceeds at a potential, some 500mV less negative than the direct electrochemical reduction. The evidence for the proposed mechanism has been obtained from theoretical simulations, using DIGISIM which shows satisfactory fitting to experimental results and allowed the determination of the rate constant for the homogeneous step. In contrast to direct reduction of RSPh where only one product, trans-1-(methoxymethoxy)-4- propoxycyclohexane (RH), has been obtained, the isolation of two products, RH and the dimer, diphenyl disulfide, PhSSPh, following mediated preparative electrolysis of RSPh, in presence of naphthalene shows that this one-electron process may be carried out at the reduction potential of naphthalene at low temperature and has also validated deductions made from voltammetric results. Copyright
