57204-95-2Relevant articles and documents
Iodine-catalyzed selective synthesis of 2-sulfanylphenols via oxidative aromatization of cyclohexanones and disulfides
Ge, Wenlei,Zhu, Xun,Wei, Yunyang
supporting information, p. 3014 - 3021 (2014/03/21)
Iodine-catalyzed intermolecular dehydrogenative aromatizations of six-membered cyclohexanones for the selective synthesis of 2-sulfanylphenols have been developed. Both aryl and alkyl disulfides can be used as sulfanylation reagents to give the desired pr
Formation of 2-phenylselenenylenones and 2-haloenones from enones. Mechanistic and synthetic aspects, X-ray crystal structures of intermediates
Engman, Lars,Toernroos, Karl Wilhelm
, p. 165 - 178 (2007/10/02)
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
Methods for the introduction of a Phenylselenium Dichloride Group into he α-position of Carbonyl Compounds. Syntheses of Enones.
Engman Lars
, p. 4031 - 4037 (2007/10/02)
Phenylselenium trichloride, PhSeCl3, direcly introduced, in fair yield, a PhSeCl2 group into the α-position of ketones with loss of HCl.To some extent, depending on the substrate, this reagent was also shown to act as a chlorinating agent toward ketones, yielding α-chloro ketones and α-phenylselenenyl ketones.The latter compounds were readily converted to selenium(IV) dichlorides by SO2Cl2 chlorination to significantly improve the overall yields of the selenetion process.The consecutive treatment of ketones with PhSeCl and SO2Cl2 could also be used for the introduction of a PhSeCl2 group, but this procedure was usually less efficient than the PhSeCl3-based one.Unsymmetrical ketones were selenated with poor regiocontrol.Aldehydes were primarily chlorinated by treatment with PhSeCl3, but consecutive treatment with PhSeCl3 and SO2Cl2 introduced a PhSeCl2 group into the α-position.Carboxylic acids and esters were ureactive toward PhSeCl3 and PhSeCl.PhSeCl3 underwent addition reactions with enones to introduce a PhSeCl2 group α or β to the carbonyl group, depending on the substrate.The carbonyl compounds substituted in the α-position with a PhSeCl2 group were easily converted to the corresponding α,β-unsaturated carbonyl compounds after hydrolysis/selenoxide elimination.Since the selenium(IV) intermediates involved were highly crustalline and easy to purify, the preparation of enones from symmetrical ketones via PhSeCl2 introduction/hydrolytic elimination was especially convenient to perform from the operational point of view.
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
Buckley, Daniel J.,McKervey, M. Anthony
, p. 2193 - 2200 (2007/10/02)
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.
SYNTHETIC APPLICATIONS OF 2-PHENYLSELENENYLENONES-III AN OVERVIEW
Liotta, Dennis,Saindane, Manohar,Barnum, Christopher,Zima, George
, p. 4881 - 4890 (2007/10/02)
2-Phenylselenenylenones are versatile species which can be selectively converted a number of different ketones and enones in high overall yields.
Reactions of α-Diazoketones with Phenylselenenyl Chloride. A new Synthesis of α-Chloro- and α-Phenylselenenyl-α,β-unsaturated Ketones
Buckley, Daniel J.,Kulkowit, Sunanta,McKervey, Anthony
, p. 506 - 507 (2007/10/02)
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
