69690-81-9Relevant academic research and scientific papers
General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium
Bieber, Lothar W.,De Sá, Ana C.P.F.,Menezes, Paulo H.,Gon?alves, Simone M.C.
, p. 4597 - 4599 (2007/10/03)
Organic halides of different structural types react with diphenyl diselenide and zinc dust in aqueous medium to give alkyl phenyl selenides. Benzylic and allylic bromides, α-bromoesters, acids and ketones and some primary alkyl iodides produce high yields even under acidic conditions. Less reactive halides need basic medium. The reaction proceeds equally well in the presence of various unprotected functional groups. Control experiments support a SH2 mechanism via alkyl radicals.
Samarium(II) Di-iodide Induced Synthesis of Allylic Phenyl Selenides from Allylic Acetates and Diphenyl Diselenide in the Presence of Palladium Catalyst
Fukuzawa, Shin-ichi,Fujinami, Tatsuo,Sakai, Shizuyoshi
, p. 927 - 930 (2007/10/02)
Allylic phenyl selenides are prepared efficiently from the reaction of allylic acetates and diphenyl diselenide induced by samarium(II) diiodide in the presence of a palladium catalyst under mild conditions.
Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines
Shea, Regan G.,Fitzner, Jeffrey N.,Fankhauser, John E.,Spaltenstein, Andreas,Carpino, Philip A.,et al.
, p. 5243 - 5252 (2007/10/02)
Oxidative rearrangement of allylic selenides in the presence of various amine nucleophiles provides synthetic access to a variety of allylic amine derivatives.The stereochemical outcome of these reactions has been investigated, and is consistent with a -sigmatropic rearrangement mechanism.Several D-α-amino acids and racemic β,γ-unsaturated α-amino acids were prepared in this manner.A variant of this process employing an achiral allylic selenide and chiral amide afforded protected allylic amines in low diastereoisomeric excess.
PREPARATION AND REACTIVITY OF α-PHENYLSELENENYL ETHERS
Goldsmith, David J.,Liotta, Dennis C.,Volmer, Mark,Hoekstra, William,Waykole, Liladhar
, p. 4873 - 4880 (2007/10/02)
α-Phenylselenenyl cyclic ethers may be prepared by the reactions of either lactols or lactol acetates with benzeneselenol, or from lactones by the "one-pot" process of reduction and Lewis acid catalyzed selenation.The tetrahydropyranyl phenyl selenides al
NOVEL SYNTHESIS OF TERTIARY ALKYL, SECONDARY AND TERTIARY BENZYL, AND ALLYL SELENIDES FROM THE CORRESPONDING ALCOHOLS
Clarembeau, M.,Krief, A.
, p. 3625 - 3628 (2007/10/02)
We report an efficient synthesis of the title compounds from alcohols and selenols.The scope and limitations of the new method are disclosed.
SYNTHESIS OF PROTECTED ALLYLIC AMINES FROM ALLYLIC PHENYL SELENIDES: IMPROVED CONDITIONS FOR THE CHLORAMINE T OXIDATION OF ALLYLIC PHENYL SELENIDES
Fankhauser, John E.,Peevey, Richard M.,Hopkins, Paul B.
, p. 15 - 18 (2007/10/02)
Anhydrous chloramine T in methanol is a highly effective reagent for the conversion of allylic phenyl selenides to the corresponding rearranged N-allylic-p-toluenesulfonamides.The reaction presumably proceeds via an allylic selenimide intermediate which undergoes -sigmatropic rearrangement.
A DIRECT PHENYLSELENENYLATION OF ALKYL HALIDES, ALKENYL SULFONATES, AND EPOXIDES BY AN ELECTROREDUCTION OF DIPHENYL DISELENIDE
Torii, Sigeru,Inokuchi, Tsutomu,Asanuma, Goro,Sayo, Noboru,Tanaka, Hideo
, p. 867 - 868 (2007/10/02)
A convenient procedure for phenylselenenylation of alkyl halides, alkenyl sulfonates, and epoxides with phenyl selenide anion was accomplished by electroreduction of diphenyl diselenide in a protic solvent.
Substitution Reactions of Thallous Thiophenoxide and Thallous Phenylselenide with Halogen-Bearing Substrates
Detty, Michael R.,Wood, Gary P.
, p. 80 - 89 (2007/10/02)
Thallous thiophenoxide (1) and thallous selenide (2) were prepared by the action of either thallous ethoxide or thallous pentoxide on thiophenol and benzeneselenol.The reagents 1 and 2 reacted readily with aroyl and acyl halides, imidoyl chlorides, α-halo ketones, α-halo esters, α-halo lactones, α-halo carboxylic acids, allyl halides, alkyl halides, chlorotrimethylsilane, chloroacetonitrile, and N-chlorosuccinimide to give substitution products and varying amounts of diphenyl disulfide and diphenyl diselenide.The reactions were run as heterogeneous mixtures in ether.The origin of the diphenyl disulfide and diphenyl diselenide was homolytic cleavage of the thallium-sulfur or thallium-selenium bond, on the basis of the products derived from the reactions of N-chlorosuccinimide with 1 and 2.
