16529-78-5Relevant academic research and scientific papers
Palladium-Catalyzed Reactions of Ketone α-Carbonates with Norbornenes. An Unusual Cyclopropanation
Ogoshi, Sensuke,Morimoto, Tsumoru,Nishio, Ken-ichi,Ohe, Kouichi,Murai, Shinji
, p. 9 - 10 (1993)
In the presence of a palladium(0) catalyst, ketone α-carbonates react with norbornene to give a cyclopropane derivative via an oxa-?-allylpalladium intermediate.
A new ruthenium-catalyzed reaction with propargyl alcohol: Cyclopropanation of norbornene
Kikuchi, Hidetoshi,Uno, Mitsunari,Takahashi, Shigetoshi
, p. 1273 - 1274 (1997)
Cationic (η5-cyclopentadienyl)tris(acetonitrile)ruthenium complexes catalyze a new reaction of propargyl alcohol with norbornene in methanol to give a cyclopropanation product, acetyltricyclooctane, in a quantitative yield.
Palladium-catalyzed α-ketocyclopropanation of norbornenes with propargyl acetates
Tanioka, Yuta,Tsukada, Naofumi
, p. 5301 - 5304 (2014/06/23)
Propargyl acetates reacted with norbornene in the presence of a catalytic amount of tetrakis(tripheylphosphine)palladium to give cyclopropyl ketones. The reaction proceeded with high stereoselectivity, affording a single stereoisomer. The reaction of various substituted norbornenes gave the corresponding cyclopropanes in moderate to good yields.
Ruthenium-catalyzed cyclopropanation of norbornene with propargyl alcohol
Matsushima, Yuji,Kikuchi, Hidetoshi,Uno, Mitsunari,Takahashi, Shigetoshi
, p. 2475 - 2482 (2007/10/03)
Norbomene as well as its 5,6-disubstituted derivatives and oxa- norbornene undergoes a novel cyclopropanation with propargyl alcohol in methanol containing cationic (η5- cyclopentadienyl)tris(acetonitrile)ruthenium complexes as catalysts to give exo-3-acetyltricyclooctane derivatives. Cyclopentadienylruthenium catalysts having an electron-withdrawing substituent on the Cp ligand exhibited the highest activity and the cyclopropanation proceeded even at -20 °C. On the basis of a deuterium labeling experiment, a reaction mechanism involving a ruthenacycle intermediate is proposed.
One-step synthesis of oxodimethylenemethane-transition metal complexes and palladium-catalyzed cycloaddition reaction
Ikeda, Isao,Ohsuka, Akihiro,Tani, Kazuyoshi,Hirao, Toshikazu,Kurosawa, Hideo
, p. 4971 - 4974 (2007/10/03)
Some alkyl allyl carbonates and an allylammonium chloride bearing (1-(butyloxy)ethyl)oxy group at the 2-position of the allyl group were synthesized and successfully transformed to oxodimethylenemethane-palladium and -platinum complexes in one step by mixing with a transition metal-(0) and triphenylphosphine. On the basis of the confirmation of vinyl ether formation by 1H NMR, the generation of oxodimethylenemethane complexes was rationalized to occur through abstraction of the β-hydrogen on the acetal carbon by an alkoxide ion which was generated from the allyl carbonate upon oxidative addition of the transition metal. The palladium-catalyzed cycloaddition of the acetonylidene group to strained olefins also proceeded successfully by using these alkyl allyl carbonates.
Regioselective cyclopropanation via unsymmetrical oxatrimethylenemethane palladium intermediates
Trost, Barry M.,Urabe, Hirokazu
, p. 615 - 618 (2007/10/02)
The mechanism of the unusual cyclopropanation of norbornenes via oxatrimethylenemethane palladium complexes is probed by regiochemical labels to establish the symmetry of the reactive intermediate.
On an (Oxatrimethylenemethane)palladium(0) Complex. An Unusual Palladium(0)-Catalyzed Cyclopropanation
Trost, Barry M.,Schneider, Stephan
, p. 4430 - 4433 (2007/10/02)
A study of the cycloadditions invoking (oxatrimethylenemethane)palladium as a transient intermediate in a catalytic cycle contrasts with the all-carbon system in giving rise to a net cycloaddition with electron-rich strained olefins rather than the
