73090-30-9Relevant academic research and scientific papers
N-Phenylselenosaccharin (NPSSac): a new electrophilic selenium-containing reagent
Tingoli, Marco,Diana, Rosita,Panunzi, Barbara
, p. 7529 - 7531 (2007/10/03)
A new reagent N-phenylselenosaccharin (NPSSac) was simply prepared and used as a source of the electrophilic phenylselenyl group. This relatively stable new compound was able to react with a series of electron rich organic molecules like alkenes in the pr
Oxidation of Diphenyl Diselenide with Ceric Ammonium Nitrate: a Novel Route for Functionalization of Olefins
Bosman, Cesare,D'Annibale, Andrea,Resta, Stefano,Trogolo, Corrado
, p. 6525 - 6528 (2007/10/02)
Alkenes were reacted with diphenyl diselenide in presence of ceric ammonium nitrate in methanol, affording β-methoxyalkyl phenyl selenides in good yields.
N-PHENYLSELENOPHTHALIMIDE (NPSP) A VALUABLE SELENENYLATING AGENT
Nicolaou, K. C.,Petasis, N. A.,Claremon, D. A.
, p. 4835 - 4842 (2007/10/02)
The phenylseleno group (PhSe) has evolved in recent years as a very useful and versatile functionality.Its facile introduction into organic molecules and its subsequent oxidative or reductive removal, has allowed many important synthetic transformations.D
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.
Factors influencing the nature of seleniranium ions in selenenyl chloride additions to alkenes: the use of methanol as solvent
Garratt, Dennis G.,Kabo, Ann
, p. 1030 - 1041 (2007/10/02)
The reaction of benzeneselenenyl chloride with some simple alkylsubstituted acyclic and cyclic alkenes has been investigated using methanol as the solvent.Products of solvent-incorporation , β-methoxyalkyl phenyl selenides, are normally favoured over the
