- α-Selective C(sp3)-H Thio/Selenocyanation of Ketones with Elemental Chalcogen
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A facile method is disclosed for the synthesis of α-thio/selenocyanato ketones through regioselective C-H thio/selenocyanation of ketones. The advantages include the use of easily available starting materials, high efficiency, simple operation, and easy scale-up. Control experiments provide evidence that the reaction proceeded via a radical way, while kinetic isotope effect experiments reveal that the cleavage of the C-H bond serves as the rate-limiting step.
- Li, Jin-Cheng,Gao, Wen-Xia,Liu, Miao-Chang,Zhou, Yun-Bing,Wu, Hua-Yue
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p. 17294 - 17306
(2021/12/02)
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- Selenocyanation of Aryl and Styryl Methyl Ketones in the Presence of Selenium Dioxide and Malononitrile: An Approach for the Synthesis of α-Carbonyl Selenocyanates
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A convenient method has been developed for the synthesis of α-carbonyl selenocyanates from aryl methyl ketones/styryl methyl ketones using selenium dioxide as the selenating agent under simple reaction conditions. This reaction has notable advantages over the traditional methods in terms of accessibility and affordability of the starting materials. The method features the interaction of aryl methyl ketones/styryl methyl ketones with selenium dioxide and malononitrile to afford a series of α-carbonyl selenocyanates in moderate to good yields.
- Marpna, Ibakyntiew D.,Wanniang, Kmendashisha,Lipon, Tyrchain Mitre,Shangpliang, O. Risuklang,Myrboh, Bekington
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p. 1980 - 1986
(2021/02/05)
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- Synthesis of Thio-/Selenopyrrolines via SnCl4-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thio-/Selenocyanates
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A straightforward protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition of aryl thio-/selenocyanates with donor-acceptor cyclopropanes (DACs) in the presence of SnCl4 as a Lewis acid catalyst. Further, good chemoselectivity was observed when DACs were treated with 3-cyano phenyl thiocyanate. These results suggest that thiocyanate is more reactive than nitrile moiety in such (3+2)-cycloaddition reactions.
- Ali, Shamsad,Goswami, Avijit,Kalaramna, Pratibha,Singh, Prasoon Raj
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supporting information
p. 4683 - 4689
(2021/09/10)
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- Solvent free nucleophilic selenocyanation with [bmim][SeCN]. Direct access to perfluoroalkylselenide compounds
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Available online-1-n-butyl-3-methylimidazolium selenocyanate ([bmim][SeCN]) proved to be a very efficient reagent for selenocyanation of alkyl halides. As part of an eco-friendly process, no organic solvents were used during the transformation and reaction times are reduced by using microwave as a heating source. The ionic liquid was carefully recycled in two different ways. Selenocyanate compounds were successfully transformed into trifluoromethylselenides in a one-pot two step procedure.
- De-Zordo Banliat, Arnaud,Grollier, Kévin,Damond, Aurélie,Billard, Thierry,Dagousset, Guillaume,Magnier, Emmanuel,Pégot, Bruce
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- Oxidative umpolung selenocyanation of ketones and arenes: An efficient protocol to the synthesis of selenocyanates
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A practical method for the umpolung selenocyanation of aryl ketones, alkyl ketones, β-ketoesters and electron-rich arenes has been developed, affording various selenocyanates in moderate to excellent yields. This transformation proceeds by an oxidative um
- Cui, Jianguo,Wei, Meizhen,Pang, Liping,Xiao, JunAn,Gan, Chunfang,Guo, Jiali,Xie, Chuanfang,Zhu, Qiming,Huang, Yanmin
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- Selenium cyanation reagent and preparation method and application thereof
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The invention discloses a selenium cyanation reagent. A structural formula thereof is as shown in the description. The selenium cyanation reagent has very good organic eletrophilicity. In the application of preparing a compound containing a selenium cyano
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Paragraph 0133-0143
(2019/02/25)
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- A novel metal-free method for the selenocyanation of aromatic ketones to afford α-carbonyl selenocyanates
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A new method has been developed for the selenocyanation of aromatic ketones. This reaction avoids the need to use pre-prepared α-halo ketones, providing rapid access to α-carbonyl selenocyanates. We also investigated the mechanism for this reaction and found that it proceeds via sequential radical iodination and nucleophilic substitution reactions.
- Sun, Kai,Lv, Yunhe,Chen, Yao,Zhou, Tingting,Xing, Yanyan,Wang, Xin
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p. 4464 - 4467
(2017/07/10)
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- Synthesis, characterization, and structures of α-substituted selenenyl-acetophenones
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A series of α-substituted selenenyl acetophenone derivatives of the types, [PhC(OCH2CH2O)CH2Se]2, [PhC(OCH2CH2O)CH2SeR], (PhCOCH2Se) 2, and [PhCOCH2/s
- Hodage, Ananda S.,Phadnis, Prasad P.,Wadawale, Amey,Priyadarsini,Jain, Vimal K.
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supporting information
p. 700 - 710
(2014/06/09)
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- Synthesis of 4-Aryl-2-imino-2H-selenazolines by a reaction of α α-(selenocyanato)acetophenones with anilines
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4-Aryl-2-imino-2H-selenazolines have been prepared by a reaction of α-(selenocyanato)acetophenones with anilines.
- Bodtke, Anja,Kandt, Madeleine,Pfeiffer, Wolf-Diethard,Langer, Peter
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p. 209 - 217
(2007/10/03)
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- Electrochemical preparation of α,α′-dicarbonylselenides
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A facile preparation of α,α′-dicarbonylselenides has been performed by reaction of α-carbonyl selenocyanates with an enolate, electrogenerated by reduction of a carbon-halogen bond.
- Otero, María Dolores,Batanero, Belen,Barba, Fructuoso
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p. 4609 - 4612
(2007/10/03)
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- A facile CAN-mediated synthesis of selenocyanates from arylalkenes and heteroarenes
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Selenocyanation of styrenes and indoles mediated by cerium(IV) ammonium nitrate (CAN) afforded the corresponding selenocyanates in moderate to good yields. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Nair, Vijay,Augustine, Anu,George, Tesmol G.
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p. 2363 - 2366
(2007/10/03)
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- Synthesis and Cycloaddition Reactivity of Selenoaldehydes
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A variety of substituted selenoaldehydes has been prepared via fluoride desilylation of α-silyl selenocyanates or base-induced elimination of HCN from simple selenocyanates containing electron-accepting or conjugating substituents.Cycloaddition reactions
- Meinke, Peter T.,Krafft, Grant A.
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p. 8671 - 8679
(2007/10/02)
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- On the Joint Reaction of Elemental Selenium with Gaseous Ammonia and Ethylenimine, respectively in the Presence of Ketones. Joint Reaction of Elementary Sulfur and Gaseous Ammonia with Ketones, 96.
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Elemental sulfur reacts with ketones and gaseous ammonia at room temperature yielding thiazoline-3 in excellent yields.Under the same conditions elemental selenium does not react at all.Attempts using the known techniques which have been applied in improving the reactivity of slowly reacting ketones in thiazoline-3-synthesis have been unsuccessful (Exp.No. 1-17).The reaction of α-halogenketones with sodiumhydrogenselenide to synthesize α-hydroselenoketones gives only the original ketones and selenium in almost quantitative yields (No. 18-23).The same is observed with α-haloketones and sodium ore magnesium-diselenides (No. 24-45).The explanation of these unexpected results is the strong reducing power of the hydrogenselenide (No. 46-52).Even α-bromoketones with activated bromine (i.g. by phenyl groups) were reduced by sodiumhydrogensulfide giving red undefinite oils.However, α-chloroketones give α-mercaptoketones in excellent yields (No. 53-61).Hydrogenselenide reduces α-mercaptoketones to sulfur and ketones in the presence of triethylamine (No. 62-67).Also the transformation of α-selenocyanketones to α,α'-diketodiselenides by alkali or the oxidative hydrolysis of selenium-"BUNTE" salts does not work and gives elementary selenium only.Studies about the concomitant reaction of elementary selenium and ethylenimine on ketones were continued (No. 68-83). - Keywords: Dihydro-p-selenazine, α-Haloketones, Hydrogenselenide reducing Action, α-Mercaptoketones
- Asinger, Friedrich,Schmitz, Maria Karoline
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p. 1191 - 1212
(2007/10/02)
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