99485-18-4Relevant academic research and scientific papers
Phenyltelluroacrylonitriles and phenylselenoacrylonitriles as precursors of (Z)-α-phenylseleno-α,β-unsaturated aldehydes, β-amino-α-phenylselenonitriles and Diels-Alder adducts
Silveira, Claudio C,Perin, Gelson,Braga, Antonio L,Dabdoub, Miguel J,Jacob, Raquel G
, p. 5953 - 5959 (2007/10/03)
Reaction of cyanomethylphosphonate with aryl selenenyl (or tellurenyl) halides and aldehydes, under basic conditions, provides α-phenylseleno or α-phenyltelluro acrylonitriles in good yields. Reaction of the α-phenylseleno acrylonitriles with dienes furnishes the corresponding adducts while reaction with amines furnishes α-phenylseleno-β-amino nitriles. Selective reduction of the cyano group with DIBAL-H results in the α-phenylseleno-α,β-unsaturated aldehydes.
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.
