- Formation of 2-phenylselenenylenones and 2-haloenones from enones. Mechanistic and synthetic aspects, X-ray crystal structures of intermediates
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The structure of trans-3-chloro-2-phenylselenenylcyclohexanone (1) was determined by X-ray diffraction.Although this and similar compounds were readily dehydrohalogenated to give vinylic selenides, they were ruled out as intermediates in the synthesis of
- Engman, Lars,Toernroos, Karl Wilhelm
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p. 165 - 178
(2007/10/02)
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- Reactions of α-Diazo Ketones with Selenium-based Reagents. A General Synthesis of α-Chloro-, α-Bromo, α-Phenylseleno-, α-Acetoxy-, and α-Methoxy-αβ-unsaturated Ketones
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Benzeneselenenyl derivatives, PhSe-X (X=Cl, Br, OCOCH3, and SCN) react readily with α-diazo ketones, RCOC(N2)R1 (R1=H or alkyl), with loss of nitrogen, furnishing αα-adducts of the type RCOCR1(X)SePh.The α-chloro and α-bromo adducts can be converted into α-methoxy adducts in methanol-sodium hydrogen carbonate.The utility of these adducts in synthesis is illustrated by their conversion (where structural considerations permit) via selenoxide fragmentation into α-heterosubstituted αβ-unsaturated ketones.Treatment of the series RCOCR1(X)SePh (R1=alkyl; X=Cl, Br, OCOCH3, and OCH3) with hydrogen peroxide-pyridine produces α-chloro-, α-bromo-, α-acetoxy-, and α-methoxy-αβ-unsaturated ketones, whereas treatment of series RCOCR1(X)SePh (R1=alkyl; X=Cl and Br) with lithium carbonate in dimethylformamide produces α-phenylseleno-αβ-unsaturated ketones.Several α-substituted cyclopentenones, cyclohexenones, and cycloheptenones have been synthesised in this way and acyclic examples are illustrated by the synthesis of 3-chloro-, 3-bromo-, 3-acetoxy-, 3-methoxy,-and 3-phenylselenobut-3-en-2-one from 3-diazobutan-2-one.
- Buckley, Daniel J.,McKervey, M. Anthony
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p. 2193 - 2200
(2007/10/02)
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- SYNTHETIC APPLICATIONS OF 2-PHENYLSELENENYLENONES-III AN OVERVIEW
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2-Phenylselenenylenones are versatile species which can be selectively converted a number of different ketones and enones in high overall yields.
- Liotta, Dennis,Saindane, Manohar,Barnum, Christopher,Zima, George
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p. 4881 - 4890
(2007/10/02)
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- Oxidation of Olefins into α-Phenylseleno Carbonyl Compounds. Highly Regioselective anti-Markownikoff Type Oxidation of Allylic Alcohol Derivatives
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By using (C6H5Se)2-t-BuOOH or (C6H5Se)(2-) (C6H5SeO)2O system, oxoselenylation reaction of C=C bonds have been examined with allylic and homoallylic alcohol derivatives, and substituted cyclohexenes, and allyl t-butyldimethylsilyl ethers are found to unde
- Shimizu, Makoto,Takeda, Ryo,Kuwajima, Isao
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p. 3510 - 3517
(2007/10/02)
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- Reactions of α-Diazoketones with Phenylselenenyl Chloride. A new Synthesis of α-Chloro- and α-Phenylselenenyl-α,β-unsaturated Ketones
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α-Diazoketones react with phenylselenenyl chloride at room temperature giving α-chloro-α-phenylselenenyl ketones; where structural considerations permit these adducts can be transformed via elimination reactions into α-chloro- or α-phenylselenenyl-α,β-uns
- Buckley, Daniel J.,Kulkowit, Sunanta,McKervey, Anthony
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p. 506 - 507
(2007/10/02)
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