98329-51-2Relevant academic research and scientific papers
Automated Electrochemical Selenenylations
Amri, Nasser,Wirth, Thomas
supporting information, p. 1751 - 1761 (2020/06/08)
Integrated electrochemical reactors in automated flow systems were utilised for selenenylation reactions. The automation allowed multiple electrochemical reactions of a programmed sequence to be performed in a fully autonomous way. Many functionalised selenenylated products were synthesised in short reaction times in good to high yields.
Catalytic chalcogenylation under greener conditions: A solvent-free sulfur- and seleno-functionalization of olefins via I2/DMSO oxidant system
Vieira, André A.,Azeredo, Juliano B.,Godoi, Marcelo,Santi, Claudio,Da Silva Júnior, Eufranio N.,Braga, Antonio L.
, p. 2120 - 2127 (2015/05/12)
Herein, we report a solvent- and metal-free methodology for the alkoxy-chalcogenylation of styrenes, using molecular iodine as a catalyst, DMSO as a stoichiometric oxidant, and different nucleophiles under microwave irradiation. This eco-friendly approach afforded the desired products in good to excellent yields in only 10 min. In addition, using the same protocol, we carried out the cyclization reaction of relevant molecules, such as lapachol derivatives.
THE REACTION O DIPHENYL DISELENIDE WITH PEROXYDISULPHATE IONS IN METHANOL A CONVENIENT PROCEDURE TO EECT THE METHOXYSELENENYLATION O ALKENES
Tiecco, M.,Testaerri, L.,Tingoli, M.,Chianelli, D.,Bartoli, D.
, p. 1417 - 1420 (2007/10/02)
Methoxyselenenylation of several alkenes was efected, in one step, by oxidation of diphenyl diselenide with ammonium peroxydisulphate in methanol.
METHOXYCHLORINATION AND DIMETHOXYLATION OF ALKENES. THE REACTIONS OF SUBSTITUTED STYRENES WITH PHENYLSELENENYL CHLORIDE IN METHANOL
Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Chianelli, Donatella,Bartoli, Donatella
, p. 2261 - 2272 (2007/10/02)
The addition of PhSeCl to α- and β-substituted styrenes in methanol is regio- and stereospecific and affords the products of methoxyselenenylation.These compounds further react with PhSeCl to give the deselenenylation products.In the case of α-substituted styrenes, 1-methoxy, 2-chloroalkanes are produced, whereas with β-substituted styrenes the major reaction products are the 1,2-dimethoxyalkanes and the 2,2-dimethoxyalkanes in which phenyl migration has occured.It is shown that these reactions proceed through the intermediate formation of the alkyl phenylselenium dichlorides, PhCR(OMe)CHR1SeCl2Ph, which evolve with different mechanisms depending on the structure of the starting alkenes.
Oxidation of Alkyl Phenyl Selenides, Tellurides, and Telluroxides with meta-Chloroperbenzoic Acid for a Facile and Novel Transformation of C-Se and C-Te Bonds to C-O Bonds
Uemura, Sakae,Fukuzawa, Shin-ichi
, p. 471 - 480 (2007/10/02)
In sharp contrast to the well-known selenoxide elimination leading to olefins, the treatment of alkyl phenyl selenides (PhSeR) with an excess of meta-chloroperbenzoic acid (MCPBA; 2-5 equiv. to a selenide) in alcohol at room temperature affords the corresponding dialkyl ethers by the substitution of a phenylselenium (PhSe) moiety with an alkoxy group.A similar reaction proceeds by using alkyl phenyl tellurides (PhTeR) and telluroxides , a facile substitution of PhTe or PhTe(O) moiety by an alkoxy group being observed.Methanol is the most appropriate solvent for these oxidations and alkyl methyl ethers are formed in excellent yields.The reaction is accompanied by phenyl migration when applied to some selenides, tellurides, and telluroxides having a phenyl group at a vicinal position to the PhSe, PhTe, or PhTe(O) moiety.Application to the methoxyselenation and methoxytelluration products of cyclohexene and cycloheptene results in a ring-contraction to afford the dimethyl acetals of cyclopentane- and cyclohexane-carbaldehyde, respectively.In case of an allylic phenyl selenide, a sigmatropic rearrangement giving a rearranged allylic alcohol occurs in much preference to the substitution by the methoxy group.Other oxidizing agents than MCPBA such as NaIO4, H2O2, t-BuOOH, and ozone are generally ineffective under similar conditions.It is proposed that the reaction mainly takes place as follows.Alkyl phenyl selenone, alkyl phenyl tellurone, or the MCPBA addition product to them is formed as a reactive intermediate in which an alkyl C-Se or alkyl C-Te bond fission occurs heterolytically by a nucleophilic attack of alcohol, sometimes accompanied by a 1,2-shift of the β-substituent, i.e., phenyl migration and ring-contraction.
