87705-48-4Relevant academic research and scientific papers
New synthesis and cyclopropanation of α-phenylselanyl α,β-unsaturated ketones with non-stabilized phosphorus ylides
Redon, Sébastien,Leleu, Stéphane,Pannecoucke, Xavier,Franck, Xavier,Outurquin, Francis
, p. 9293 - 9304 (2008/12/22)
A general method for the preparation of α-phenylselanyl enones is described. Phosphorus ylides react with these α-phenylselanyl enones in a 1,4-addition, leading to cyclopropanes and/or dihydrofurans, depending on the substitution pattern. This unusual reactivity is due to the phenylselanyl moiety, hindering the carbonyl of the enone and making it less prone to 1,2-additions or promoting conjugate addition by electronic effects.
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.
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 (
