99484-77-2Relevant academic research and scientific papers
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.
The Binary Reagent PhSeCl-ZnCl2: a Powerful Chloro-Phenylselenenylating Agent of Electrophilic Olefins
D'Onofrio, Franco,Parlanti, Luca,Piancatelli, Giovanni
, p. 1929 - 1932 (2007/10/02)
The binary reagent PhSeCl-ZnCl2 was found to be powerful for the stereocontrolled conversion of highly electrophilic olefins, such as maleate and fumarate esters, into the corresponding chloro phenylseleno derivatives in very high yields.Other olefins, su
Electrophilic Addition of Benzeneselenenyl Chloride to Alkenes Bearing an Electron-withdrawing Substituent
Toshimitsu, Akio,Terao, Keiji,Uemura, Sakae
, p. 1059 - 1062 (2007/10/02)
Reaction of benzeneselenenyl chloride with alkenes bearing electron-withdrawing substituents was found to afford a mixture of regioisomeric adducts formed via the electrophilic addition of the phenylseleno group.The isomer distribution can be accounted for by postulating the interaction in the episelenonium ion intermediate of the phenylseleno group with the electron-withdrawing substituent.
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.
