102052-40-4Relevant academic research and scientific papers
Reactions of electron-withdrawing thiophene 1,1-dioxides with furans. A novel reaction pathway
Moiseev,Balenkova,Nenajdenko
, p. 712 - 717 (2006)
Reactions of thiophene dioxides containing electron-withdrawing substituents with furans were studied. The reactions with unsubstituted furan followed the inverse-electron-demand Diels-Alder mechanism. Subsequent elimination of sulfur dioxide from the add
Janovsky reactions between cyclopentadienyliron complexes of substituted benzenes and carbanions derived from ketones
Sutherland, Ronald G.,Chowdhury, Ratan L.,Piorko, Adam,Lee, Choi Chuck
, p. 2031 - 2037 (2007/10/02)
Janovsky reactions were carried out between various η6-substituted benzene-η5-cyclopentadienyliron cations containing at least one electron-withdrawing substituent in the complexed arene and enolate-carbanion derived from acetone, butanone, or 3-pentanone.Highly colored adducts were obtained from reactions of the cyclopentadienyliron (CpFe) complexes of nitrobenzene, cyanobenzene, p-tolylsulfonylbenzene, benzoylbenzene, o-, p-, or m-toluene, and o-, p-, or m-dichlorobenzene with acetone in aqueous KOH, the products being derived from exo-addition of the acetonyl anion regioselectively at a position ortho to an electron-withdrawing substituent.For example, reaction of the η6-nitrobenzene-η5-cyclopentadienyliron cation (1a) with acetone in aqueous KOH gave (R,S)-(1-5-η5-1-nitro-6-exo-(2-oxo-1-propyl)cyclohexadienyl)(η5-cyclopentadienyl)iron (2a), isolated as a purple solid.Similarly, recation of the nitrobenzene complex 1a with 3-pentanone in aqueous KOH gave two diastereomeric adducts. (R,R-S,S)- and (R,S-S,R)-1-5-η5-1-nitro-6-exo-(3-oxo-2-pentyl)-cyclohexadienyl)(η5-cyclopentadienyl)ironb (11a, b).Reactions of the CpFe complexes of chlorobenzene and o- or p- dichlorobenzene with butanone in aqueous KOH were also investigated.In each case, three Janovsky adducts, two being diastereomers, were obtained from addition of the two carbanions derived from loss of either α-proton of butanone.Potential synthetic applications via these Janovsky adducts are pointed out since their treatment with ammonium ceric nitrate could lead to demetallation-oxidation; for example. (2,5-dichlorophenyl)propanone,, a new compound, was obtained from the adduct formed between the p-dichlorobenzene complex and the acetonyl anion.
Yanovsky Reaction of η6-Arene-η5-cyclopentadienyliron Cations with Carbanions derived from Ketones. Regiospecific Attack ortho to Electron Withdrawing Functions
Sutherland, Ronald G.,Chowdhury, Ratan L.,Piorko, Adam,Lee, Choi Chuck
, p. 1296 - 1297 (2007/10/02)
η6-Arene-η5-cyclopentadienyliron salts containing electron withdrawing groups such as nitro, halogeno, benzoyl, cyano, and sulphonyl on the arene ring react with carbanions to give electroneutral adducts of the Yanovsky type; these a
