61713-63-1Relevant academic research and scientific papers
Meyer-Schuster-Type Rearrangement of Propargylic Alcohols into α-Selenoenals and -enones with Diselenides
Ban, Yong-Liang,You, Long,Feng, Kai-Wen,Ma, Fei-Cen,Jin, Xiao-Ling,Liu, Qiang
, p. 5274 - 5283 (2021/04/06)
We describe a mild and broadly applicable protocol for the preparation of a diverse array of multisubstituted α-selenoenals and -enones from readily accessible propargylic alcohols and diselenides. The transformation proceeds via the Selectfluor-promoted selenirenium pathway, which enables selenenylation/rearrangement of a variety of propargylic alcohols. Gram-scale experiments showed the potential of this synergistic protocol for practical application.
A radical cyclization route to pyrrolidines based on conjugate addition to electron deficient phenylselenenylalkenes
Berlin, Stefan,Engman, Lars
, p. 3701 - 3704 (2007/10/03)
α-Phenylselenenyl-α,β-unsaturated esters, amides, ketones, nitriles and sulfones were prepared by zinc chloride promoted chloroselenation/dehydrochlorination of the corresponding α,β-unsaturated compounds. After Michael addition of allyl or propargylamine and triethylborane initiated reductive radical cyclization in the presence of tris(trimethylsilyl)silane, pyrrolidine and dihydropyrrole derivatives, respectively, were obtained. (C) 2000 Elsevier Science Ltd.
Allylic and Propargylic Phenyl Selenide Oxygenation by Cyclohexanone Oxygenase: -Sigmatropic Rearrangement of the Enzyme-generated Selenoxide
Latham, John A.,Branchaud, Bruce P.,Chen, Y.-C. Jack,Walsh, Christopher
, p. 528 - 530 (2007/10/02)
Enzymic oxidation of propargylic and allylic selenides has been carried out and the resulting selenoxides found to readily undergo 2,3-sigmatropic rearrangement; the propargylic product undergoes fragmentation while the allylic product yields racemic alcohols.
Preparations de composes α-arylselenocarbonyles a l'aide de morpholinoareneselenenamides
Lerouge, Patrice,Paulmier, Claude
, p. 1219 - 1224 (2007/10/02)
The reactivity of the morpholinoareneselenenamides 1 which are readily prepared from various diaryldiselenides, is investigated.The selenenamides 1 are good α-selenenylating agents for aliphatic aldehydes, α-ketoesters and conjugated enals yielding the α-
CAPTODATIVE SUBSTITUENT EFFECTS XXI. SYNTHESIS OF SELENENYLATED CAPTODATIVE OLEFINS VIA SELENENYL HALIDE ADDITION TO OLEFINS BEARING ELECTRON-WITHDRAWING SUBSTITUENTS
Piettre, S.,Janousek, Z.,Merenyi, R.,Viehe, H. G.
, p. 2527 - 2544 (2007/10/02)
Addition of methane- and benzeneselenenyl bromide or chloride and benzene sulfenyl chloride to carbon-carbon double bonds substituted by electron-withdrawing groups is achieved in solvents of different polarity.Two regioisomeric adducts 6 and 7 or 8 and 9 are generally formed, which can be interconverted by equilibration in refluxing acetonitrile.It is of mechanistic interest that the regioisomers may also derive from selenenyltrihalide adducts.In comparison to acrylic esters, the propiolic ester reacts more slowly, producing mainly the α-selenenyl adduct.Dehydrohalogenation of adducts provides a general and valuable method for the preparation of olefins carrying methyl or phenylselenyl groups in α-position to electron-withdrawing substituents.
SYNTHESE D'α-HYDROXYALLENES α-FONCTIONNALISES A PARTIR D'α-PHENYLSELENOENALS
Lerouge, Patrice,Paulmier, Claude
, p. 1987 - 1990 (2007/10/02)
Morpholinobenzeneselenenamide (MBSe) react with enals to form α-phenylselenoenals which undergo Wittig and Horner reactions.We synthetise 1-substituted 3-phenylseleno-1,3-butadienes.Oxidation and subsequent 2,3-sigmatropic rearrangement lead to α-fonctionnalized α-hydroxyallenes.This compounds give access to 2,5 dihydrofurans.
CAPTO-DATIVE SUBSTITUENT EFFECTS XIII. C4-BRIDGED RADICAL DIMERISATION WITH α-PHENYLSELENOACRYLIC ACID DERIVATIVES
Janousek, Z.,Piettre, S.,Gorissen-Hervens, F.,Viehe, H.G.
, p. 197 - 202 (2007/10/02)
Several capto-dative olefins containing the phenylselenenyl group have been obtained via selenenyl halide addition to acrylic derivatives followed by halide elimination.Some of the olefins efficiently trap the radicals formed from azobisisobutyronitrile (
