99485-12-8Relevant 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 (2000)
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.
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.
