96095-49-7Relevant academic research and scientific papers
Rhodium-Catalyzed Intermolecular Carbonylative [2 + 2 + 1] Cycloaddition of Alkynes Using Alcohol as the Carbon Monoxide Source for the Formation of Cyclopentenones
Kim, Ju Hyun,Song, Taemoon,Chung, Young Keun
, p. 1248 - 1251 (2017)
A highly regioselective rhodium-catalyzed intermolecular carbonylative [2 + 2 + 1] cycloaddition of alkynes using alcohol as a CO surrogate to access 4-methylene-2-cyclopenten-1-ones has been developed. In this transformation, the alcohol performs multiple roles, including generating the Rh-H intermediate, functioning as the CO source, and assisting in the isomerization of the alkyne. Alkynes can act as both the olefin and the alkyne partner in the cyclopentenone core.
Stereoselective synthesis of (E)-4-alkylidenecyclopent-2-en-1-ones by a tandem ring closure-Michael addition-elimination
Ballini, Roberta,Bosica, Giovanna,Fiorini, Dennis,Gil, Maria Victoria,Petrini, Marino
, p. 1265 - 1267 (2007/10/03)
(equation presented) Reaction of (Z)-1,4-diketones with various functionalized nitroalkanes in the presence of DBU gives 4-alkylidenecyclopent-2-en-1-ones with E selectivity. A cyclopentadienone intermediate is probably formed by intramolecular aldol cond
Study of the Reactions of Substituted Allenes with Tris(triphenylphosphine)nickel(0). An Analysis of the Factors Affecting the Regio- and Stereochemistry of ?-Complex Formation and Coupling To Form Nickelacyclopentane Complexes
Pasto, Daniel J.,Huang, Nai-Zhong,Eigenbrot, Charles W.
, p. 3160 - 3172 (2007/10/02)
The reactions of ethylallene (ETA), tert-butylallene (TBA), phenylallene (PHA), cyanoallene (CYA), and methxoyallene (MEA) with tris(triphenylphosphine)nickel(0) have been investigated and compared with the reaction of dimethylallene (DMA) with (TPP)3Ni reported earlier.At low temperatures ( PHA > MEA >> DMA > ETA > TBA.Evidence for a competitive electron-transfer process with CYA is presented.The structures of the intermediate substituted nickelacyclopentane complexes are inferred from the structures of the hydrocarbon products formed in reductive-elimination and hydrogen-migration, reductive-elimination reactions and from the structures of ketonic products formed on reaction with carbon monoxide.Specific ?-?, ?-?, and ?-? modes of coupling in syn and anti conformations of the bis-?-complexes have been identified.The regio- and stereochemistry of formation of the nickelacyclopentane ?-complexes are discussed in terms of steric and electronic (orbital energy and AO coefficients) effects in the rate-determining transition state for ?-complex formation.
