63603-32-7Relevant 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.
Oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). A new method for the electrophilic phenylselenenylation of alkenes under mild conditions
Tiecco,Testaferri,Temperini,Bagnoli,Marini,Santi
, p. 1767 - 1771 (2007/10/03)
The oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) represents a convenient mild method to produce a strongly electrophilic phenylselenium reagent. Clean phenylseleno methoxylations and hydroxylations of alkenes containing different types of functional groups can be effected by working in methanol or in acetonitrile and water, respectively. This new electrophilic reagent can also be employed to promote efficient cyclization reactions of alkenols to tetrahydrofurans or of alkenoic acids to lactones.
Novel Method for Electrophilic Selenenylation Using Diselenide with Nitrobenzenesulfonyl Peroxide
Yoshida, Masato,Satoh, Naomi,Kamigata, Nobumasa
, p. 1433 - 1436 (2007/10/02)
Diphenyl diselenide could be readily converted into cationic selenenylating reagent by treating with m-nitrobenzenesulfonyl peroxide, and the intermediate was reacted with olefins in the presence of methanol, phenol, or electorn-rich benzenes in one pot to afford methoxy-, phenoxy-, or arylselenenylated compounds, respectively.
A halide ion promoted electrochemical oxyselenenylation of olefins
Torii, Sigeru,Uneyama, Kenji,Ono, Michio
, p. 2741 - 2744 (2007/10/02)
A novel electrolytic transformation of olefins 1 into oxyselenides 2 has been performed in high yields and high regioselectivities by elctrolyzing olefins in protic solvents (MeOH, AcOH, H2O-MeCN) containing Et4NX (X = Cl, Br, I) and diphenyl diselenide using platinum foils.
Facile Oxyselenation of Olefins in the Presence of Copper(II) or Copper(I) Chloride as Catalyst
Toshimitsu, Akio,Aoai, Toshiaki,Uemura, Sakae,Okano, Masaya
, p. 1953 - 1958 (2007/10/02)
Treatment of olefinic hydrocarbons with phenyl selenocyanate in alcohol in the presence of copper(II) or copper(I) chloride affords β-alkoxyalkyl phenyl selenide in good yield.Similar reactions in aqueous tetrahydrofuran or acetic acid-chloroform give the corresponding selenide.The reaction is trans stereospecific in the cases of trans-2-butene, cis-2-butene, and cyclohexene and regiospecific in the cases of styrene, acrylaldehyde, crotonaldehyde, and vinylacetate, respectively.The reaction proceeds even with a catalytic amount of copper(II) chloride.Of the various transition-metal salts examined, nickel(II) halides are similar to copper(II) or copper(I) halides as catalyst; the chlorides of Cr(III) and Co(II) are moderately effective, while the chlorides of Mn(II), Fe(III), Fe(II), Zn(II), Ag(I), Cd(II), Hg(II), Hg(I), Tl(III), and Tl(I) are almost ineffective.The use of the pyridine complex of copper or nickel halides suppresses the reaction.The reaction is presumed to proceed via (i) the polarization of the Se-CN bond by coordination of the effective metal salt to the cyano group and (ii) a nucleophilic attack of olefin on the polarized selenium.The substituent parameters of phenylseleno and selenocyanato groups for 13C NMR have been found to be +13 and +15 to 16 ppm for the α carbon and +6 and +6 to 7 ppm for the β carbon, respectively.
