95391-78-9Relevant academic research and scientific papers
Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
Heredia, Adrián A.,Pe?é?ory, Alicia B.
, p. 105699 - 105706 (2015/12/26)
A simple procedure for the synthesis of alkyl styryl selenides was developed. This methodology involves the in situ generation of selenolate anions by a one-pot and three-step protocol where a nucleophilic substitution between KSeCN and alkyl halides affords the corresponding alkyl selenocyanate in the first step, giving dialkyl diselenide by a further K3PO4-assisted reaction. Subsequent reduction yields the alkyl selenolate anions which react with substituted (E,Z)-β-styryl halides to afford the corresponding vinyl selenides with retention of stereochemistry and from moderate to excellent yields. This procedure does not require a catalyst, proceeds under an air atmosphere and within a short reaction time, and is free from diselenide and malodorous and air-sensitive alkyl selenols as starting materials.
Thermal reactions of phenylacetylene with a mixture of thiophenol and dialkyl diselenide
Shilkina,Papernaya,Deryagina,Albanov
, p. 1256 - 1258 (2007/10/03)
Heating to phenylacetylene with a mixture of thiophenol and dialkyl diselenide to 150-180°C yields previously unknown products of simultaneous addition to the phenylacetylene triple bond of alkylselenyl and phenthiyl groups, 2-alkylselenyl-1-phenyl-1-phenylthioethenes. The free-radical reaction mechanism is discussed.
Nickel and Palladium Catalysed Coupling of Vinyl Selenides with Trimethylsilylmethylmagnesium Chloride: A New Synthesis of Allyl Silanes
Hevesi, Laszlo,Hermans, Bernard,Allard, Christophe
, p. 6729 - 6730 (2007/10/02)
A new access to allyl silanes by the Ni and Pd catalysed cross-coupling reactions of vinyl selenides and trimethylsilylmethylmagnesium chloride (DME/Rfx/65-83percent yield) is reported.
STEREOSPECIFIC SYNTHESIS OF DIVINYL DISELENIDES FROM VINYL ACETYL SELENIDES
Testaferri, Lorenzo,Tiecco, Marcello,Chianelli, Donatella,Tingoli, Marco
, p. 4577 - 4584 (2007/10/02)
Vinyl halides react with MeSeLi in DMF to afford vinyl methyl selenides which are demethylated by the excess of the MeSeLi; the vinyl selenide anions thus obtained react with acetyl chloride to give vinyl acetyl selenides.This three steps one pot synthesis occurs with complete retention of configuration.The vinyl acetyl selenides are cleanly fragmented by electron transfer to the vinyl selenide anions; addition of iodine to the resulting solutions produced the divinyl diselenides with retention of configuration.The transformation of vinyl acetyl selenides into divinyl diselenides can also be induced by catalytic amounts of a solution of sodium in HMPA or of sodium methanethiolate.
NEW SYNTHESIS OF VINYL SELENIDES NUCLEOPHILIC SUBSTITUTIONS OF UNACTIVATED VINYL HALIDES BY SELENIDE ANIONS
Tiecco, M.,Testaferri, L.,Tingoli, M.,Chianelli, D.,Montanucci, M.
, p. 4975 - 4978 (2007/10/02)
Alkyl and aryl selenide anions react with unactivated vinyl halides, in dipolar aprotic solvents, to give alkyl or aryl vinyl selenides in good yields.These reactions are stereospecific and occur with retention of configuration.
