51364-92-2Relevant academic research and scientific papers
General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium
Bieber, Lothar W.,De Sá, Ana C.P.F.,Menezes, Paulo H.,Gon?alves, Simone M.C.
, p. 4597 - 4599 (2001)
Organic halides of different structural types react with diphenyl diselenide and zinc dust in aqueous medium to give alkyl phenyl selenides. Benzylic and allylic bromides, α-bromoesters, acids and ketones and some primary alkyl iodides produce high yields even under acidic conditions. Less reactive halides need basic medium. The reaction proceeds equally well in the presence of various unprotected functional groups. Control experiments support a SH2 mechanism via alkyl radicals.
Preparation and oxidation of α-phenylselanyl esters
Lebarillier, Loic,Outurquin, Francis,Paulmier, Claude
, p. 7483 - 7493 (2007/10/03)
Alkylation and selenenylation of selenium-stabilized ester enolates have allowed the preparation of α-phenylselanyl esters 5, 7, 8 and of α,α-bis(phenylselanyl)esters 6, respectively. The competitive selenophilic reaction, leading to an allylic phenylselenide 9, was avoided in the presence of HMPA. α-phenylselanyl α,β-unsaturated esters 15 were prepared by oxidation of compounds 6 and dehydrohalogenation of β-chloroesters 17. Some other transformations: oxidation, transesterification and Grignard reaction were also studied. H2O2 oxidation of Z-esters 15 has led to stable E-α-seleninyl esters 20. (C) 2000 Elsevier Science Ltd.
