70187-90-5Relevant academic research and scientific papers
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
PHENYLSELENENYL CHLORIDE IN ACETONITRILE-WATER; A HIGHLY CONVENIENT REAGENT FOR HYDROXYSELENATION OF OLEFINS AND PREPARATION OF CYCLIC ETHERS FROM DIENES
Toshimitsu, Akio,Aoai, Toshiaki,Owada, Hiroto,Uemura, Sakae,Okano, Masaya
, p. 5301 - 5306 (2007/10/02)
The reaction of phenylselenenyl chloride with olefins in aqueous acetonitrile affords β-hydroxyalkyl phenyl selenides in excellent yields, providing the most convenient method for hydroxyselenation of olefins so far reported.When the reaction was applied to conjugated dienes, monohydroxyselenated products were obtained in good to excellent yields.From non-conjugated dienes, on the other hand, cyclic ethers containing two phenylseleno groups were produced in good to excellent yields, the first step of this reaction being the hydroxyselenation of one double bond.
Oxyselenation of Diolefins with Phenyl Selenocyanate and Cooper(II) Chloride. Synthesis of Cyclic Ethers
Toshimitsu, Akio,Aoai, Toshiaki,Uemura, Sakae,Okano, Masaya
, p. 3021 - 3026 (2007/10/02)
A general route for cyclic ethers by oxyselenation of diolefins is described.Reaction of cis,cis-1,5-cyclooctadiene with phenyl selenocyanate in the presence of copper(II) chloride in various alcohols, aqueous tetrahydrofuran, or aqueous acetonitrile produces an isomeric mixture of 2,6-bis(phenylseleno)-9-oxabicyclononane (1a) and 2,5-bis(phenylseleno)-9-oxabicyclononane (1b) in a good to excellent yield.The isomer ratio depends on the solvent utilized, and a suitable choice of solvent results in a selective formation of each isomer.Similar treatment of 5-methoxy- and 5-hydroxycyclooctenes also gives an isomeric mixture of 2-(phenylseleno)-9-oxabicyclononane (4a) and its isomer (4b). 13C NMR spectral data reveal that all phenylseleno groups are on an endo position of the bicyclic ring system in 1a,b and 4a,b, consistent with the trans stereospecificity of the oxyselenation reaction.The application to other diolefins such as 1,5-hexadiene, diallyl ether, diallyl sulfide, or 4-vinylcyclohexene in aqueous acetonitrile as solvent results in the formation of monocyclic and bicyclic ethers bearing two phenylseleno groups (5-8) in good to excellent yields.The reaction proceeds through alkoxy- or hydroxyselenation of one double bond, followed by a transannular attack of the alkoxyl or hydroxyl group on the episelenonium ion which is formed at the other double bond by the attack of another phenyl selenocyanate.
