- CeCl3/Sm system induced reductive cleavage of the Se-Se bond in diaryl diselenides: A novel method for the synthesis of β-selenoesters and β-selenonitriles
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The Se-Se bond in diselenides was reduced by CeCl3/Sm system to produce selenolate anions, which react with α,β-unsaturated esters or α,β-unsaturated nitriles to afford β-selenoesters and β-selenonitriles, respectively.
- Li, Xue,Zhang, Songlin,Wang, Yulu,Zhang, Yongmin
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- A convenient synthesis of β-phenylselenocarbonyl compounds by In-TMSCL promoted cleavage of diphenyl diselenide and subsequent michael addition
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A simple and convenient procedure has been developed for the synthesis of β-phenylselenocarbonyl compounds by a one-pot reaction of diphenyl diselenide and α,β-unsaturated ketones, aldehydes, esters and nitriles in the presence of indium metal-trimethylsilyl chloride under sonication. Presumably, the In-TMSCl reagent system reacts with diphenyl diselenide to form an intermediate, PhSeSiMe3, which then undergoes Michael addition with the α,β-unsaturated carbonyl compounds to produce the products.
- Ranu, Brindaban C.,Das, Arijit
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- β-Cyclodextrin-promoted addition of benzeneselenol to conjugated alkenes in water
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For the first time, a mild and efficient procedure was developed for the conjugate addition of α,β-unsaturated compounds to benzeneselenol providing β-(phenylseleno)-substituted compounds (Scheme). The reaction was promoted by β-cyclodextrin, proceeded in
- Srinivas, Boga,Kumar, Vydyula Pavan,Sridhar, Regati,Reddy, Vutukuri Prakash,Nageswar, Yadavalli Venkata Durga,Rao, Kakulapati Rama
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experimental part
p. 1080 - 1084
(2009/10/17)
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- An efficient route to vinyl substituted oxadiazoles and triazoles using phenylselanyl derivatives as precursor
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Vinyl substituted oxadiazoles and triazoles were obtained from selenoxide syn-elimination of phenylselanylethyl substituted oxadiazoles and triazoles, which were prepared through hydrazinolysis, acylation, and cyclocondensation reactions of phenylselanyl-
- Wang, Yu-Guang,Huang, Xian,Wu, Yu-Zhou
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p. 7866 - 7873
(2008/02/08)
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- Convenient preparation of benzylseleno- and phenylselenoalkanoic acids: Reagents for synthesis of organoselenium compounds
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An efficient and operationally simple route to benzylseleno- and phenylselenoalkanoic acids from ethyl benzyl/phenylselenoalkanoates is described. This involves preparation of ethyl benzyl/phenylselenoalkanoates as substrates by reaction of dibenzyl/diphenyl diselenide and sodium borohydride with ethyl chloroalkanoates in ethanol followed by basic hydrolysis and subsequent acidification. Copyright Taylor & Francis Group, LLC.
- Bhalla, Aman,Sharma, Sitansh,Bhasin, Kuldip K.,Bari, Shamsher S.
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p. 783 - 793
(2007/10/03)
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- Zn/RuCl3-promoted cleavage of diselenides: An efficient michael addition of zinc selenolates to conjugated alkenes in aqueous media
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A simple and highly efficient one-pot route to β-selenocarbonyl compounds and nitriles has been developed by Zn/RuCl3-catalyzed cleavage of diselenides and subsequent Michael addition of zinc selenolates to conjugated alkenes in aqueous media. Georg Thieme Verlag Stuttgart.
- Movassagh, Barahman,Tatar, Ameneh
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p. 1954 - 1956
(2008/03/28)
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- One-pot synthetic method of unsymmetrical diorganyl selenides: Reaction of diphenyl diselenide with alkyl halides in the presence of lanthanum metal
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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
- Nishino, Toshiki,Okada, Mitsuo,Kuroki, Takamasa,Watanabe, Toshihisa,Nishiyama, Yutaka,Sonoda, Noboru
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p. 8696 - 8698
(2007/10/03)
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- General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium
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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.
- Bieber, Lothar W.,De Sá, Ana C.P.F.,Menezes, Paulo H.,Gon?alves, Simone M.C.
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p. 4597 - 4599
(2007/10/03)
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- Synthesis of chalcogenides using indium intermediates in aqueous media
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Selenides and vinylic selenides were synthesized from their corresponding organic halides and alkynes in aqueous media using indium metal.
- Galindo, Andréa C.,Oliveira, Juliana M.,Barboza, Maria A. G.,Gon?alves, Simone M. C.,Menezes, Paulo H.
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p. 129 - 140
(2007/10/03)
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- Zn/Zrcl4 system induced reductive cleavage of the Se-Se bond in diaryl diselenides: A novel method for the synthesis of β-selenoesters and β-selenonitriles
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The Se-Se bond in diselenides was reduced by Zn/ZrCl4 to produce selenolate anions, which react with α,β-unsaturated esters or α,β-unsaturated nitriles to afford β-selenoesters and β-selenonitriles, respectively.
- Zhang,Tian
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p. 198 - 199
(2007/10/03)
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- An effective synthesis of β- selenium and β-tellurium carbonyl compounds via reaction of diaryldiselenides or diarylditellurides with α,β- unsaturated carbonyl compounds induced by low-valent titanium
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β-Selenium and β-tellurium carbonyl compounds have been prepared in good yield by reaction of diaryldiselenides or diarylditelluride with α,β- unsaturated carbonyl compounds induced by TiCl4 / Sm/THF system under mild reaction conditions.
- Zhou, Long-Hu,Zhang, Yong-Min
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p. 533 - 540
(2007/10/03)
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- Direct Preparation of Lanthanoid Ester Homoenolates from 3-Halo Esters and Lanthanoid Metals: Their Homo-Reformatsky-Type Reaction with Carbonyl Compounds
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The direct reaction of ethyl 3-bromopropionate (2a) or 3-iodopropionate (2b) with lanthanoid metals (La, Ce, Nd, Sm) in tetrahydrofuran produces lanthanoid ester homoenolates (3), which react with ketones to give γ-lactones in good yields under mild conditions.The isolation of 3-phenylseleno (8a), 3-phenyltelluro (8b), and 3-tri-n-butylstannyl esters (10) from the reaction with diphenyl diselenide (7a), ditelluride (7b), and tri-n-butyltin iodide (9), respectively, suggests the formation of the lanthanoid ester homoenolate.
- Fukuzawa, Shin-ichi,Sumimoto, Norifumi,Fujinami, Tatsuo,Sakai, Shizuyoshi
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p. 1628 - 1631
(2007/10/02)
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- o-Quinodimethane Generation from α,α'-Dihalo-o-xylenes by Use of Sodium Benzenetellurolate
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Treatment of α,α'-dihalo-o-xylenes with sodium benzenetellurolate gave o-quinodimethane which readily reacted with dienophiles leading to Diels-Alder adducts.The best yields were obtained when the reaction was carried out in refluxing ethanol using two molar equivalents of the benzenetellurolate to α,α'-dihalo-o-xylenes.This reaction competes with substitution of the halogen atoms with the benzenetellurolate anion to afford α,α'-bis(phenyltelluro)-o-xylene, which did not give o-quinodimethane under identical conditions.It is likely that the reaction proceeds through nucleophilic attack of benzenetellurolate anion at the tellurium atom of α-halo-α'-phenyltelluro-o-xylene which is formed in situ by the substitution of one of the halogen atoms of the starting α,α'-dihalo-o-xylene with the benzenetellurolate anion.When sodium benzeneselenolate was employed, no evidence of o-quinodimethane formation was observed under similar conditions.
- Kambe, Nobuaki,Tsukamoto, Takashi,Miyoshi, Noritaka,Murai, Shinji,Sonoda, Noboru
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p. 3013 - 3018
(2007/10/02)
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