17417-82-2Relevant academic research and scientific papers
One-pot synthetic method of unsymmetrical diorganyl selenides: Reaction of diphenyl diselenide with alkyl halides in the presence of lanthanum metal
Nishino, Toshiki,Okada, Mitsuo,Kuroki, Takamasa,Watanabe, Toshihisa,Nishiyama, Yutaka,Sonoda, Noboru
, p. 8696 - 8698 (2002)
A convenient synthetic method of unsymmetrical selenides has been developed. When diphenyl diselenide was allowed to react with two equimolar amounts of primary alkyl iodides and bromides in the presence of an equimolar amount of lanthanum metal, alkyl ph
A novel and highly efficient synthetic route to unsymmetrical organoselenides using cesium bases
Cohen, Richard J.,Fox, Daniel L.,Salvatore, Ralph Nicholas
, p. 4265 - 4268 (2007/10/03)
A new and convenient one-pot method for the preparation of unsymmetrical selenides has been developed. In the presence of cesium hydroxide, molecular sieves, and DMF, benzeneselenol undergoes direct alkylation with various alkyl halides for the synthesis of alkyl phenyl selenides in moderate to excellent yields. Another method to prepare unsymmetrical organoselenides was also completed by coupling terminal alkynes with benzeneselenyl bromide. As an application, the synthesis of a selenopeptide was also accomplished. Furthermore, this methodology was extended to the synthesis of an organoselenide on solid support.
SH2' Type Reactions of Arenesulfonyl Chlorides with Allylic Compounds Catalyzed by a Ruthenium(II) Complex
Kamigata, Nobumasa,Ishii, Kimiko,Ohtsuka, Takeshi,Matsuyama, Haruo
, p. 3479 - 3481 (2007/10/02)
In the presence of a catalytic amount of dichlorotris(triphenylphosphine)ruthenium(II), the reactions of arenesulfonyl chlorides with allyl phenyl sulfide and allyl phenyl selenide proceeded smoothly to give allyl phenyl sulfone in high yield as well as the corresponding diphenyl disulfide or diphenyl diselenide.An SH2'-type mechanism involving the arenesulfonyl radical is proposed.
Vinyl Selenides and Selenoxides: Preparation, Conversion to Lithium Reagents, Diels-Alder Reactivity, and Some Comparisons with Sulfur Analogues
Reich, Hans J.,Willis, William W.,Clark, Peter D.
, p. 2775 - 2784 (2007/10/02)
A variety of aryl vinyl selenides are prepared by reaction of vinyl Grignard reagents with aryl selenyl bromides or by reductive elimination of the adducts of lithiums with carbonyl compounds.Deprotonation of phenyl vinyl selenide is achieved with LDA at -78 deg C in THF.Vinyl selenides with β-alkyl groups require LiTMP and warmer temperatures (-50 deg C) for complete deprotonation.Allylic lithium reagents were obtained from 1-propenyl and 2-methyl-1-propenyl selenides whereas 1-butenyl or 3-methyl-1-butenyl selenides gave vinyl lithium reagents.Reaction with electrophiles proceeds in good to excellent yield.Primary halides require HMPA to react well.Unhindered carbonyl compounds react without enolization.Deprotonation with LDA is shown to be reversible, and during competitive deprotonation studies with LDA, aryl vinyl sulfides are found to be thermodynamically less acidic than aryl vinyl selenides (KS/Se=0.21 for phenyl vinyl and 0.3 for m-(trifluoromethyl)phenyl vinyl).Deprotonation with LiTMP is shown to be irreversible, and competitive deprotonation studies showed vinyl selenide to be kinetically more acidic as well S/Se=0.37 (phenyl vinyl),0.42 (m-(trifluoromethyl)phenyl vinyl)>.Most studies have shown sulfur compounds to be more acidic. m-(Trifluoromethyl)phenyl allyl sulfide as expected, is more acidic than selenium compound (kS/Se=3.8).Vinyl selenoxides can be prepared with m-chloroperbenzoic acid.They are not thermally stable enough to serve as acetylene equivalents in Diels-Alder reactions.Phenyl vinyl selenide gives a Diels-Alder addition product with 1,4-diphenylisobenzofuran but failed to give cycloaddition products with less reactive dienes.Phenyl vinyl selenoxide does not give a useful yield of lithium reagent upon reaction with amide bases.
