Search results for "Cyclopentene"
showing 10 items of 17 documents
Rhodium(III)-catalyzed ring-opening of strained olefins through C–H activation of O-acetyl ketoximes: an efficient synthesis of trans-functionalized …
2013
An efficient strategy for the stereoselective synthesis of functionalized cyclopentenes and spiro[2.4]heptenes from strained olefins via C–H activation of aryl ketone O-acetyl ketoximes using [RhCl2Cp∗]2 catalyst is described. The results revealed that a wide range of readily accessible aryl and heteroaryl ketoximes are compatible in this method for the ring opening of bicyclic and spirotricyclic olefins.
Understanding the mechanism of stereoselective synthesis of cyclopentenes via N-heterocyclic carbene catalyzed reactions of enals with enones.
2010
The N-heterocyclic carbene (NHC) catalyzed addition of enals to enones to yield trans-cyclopentenes has been investigated using DFT methods at B3LYP/6-31G** computational level. This NHC catalyzed reaction comprises several steps. The first one is the formation of a Breslow intermediate, which nucleophilically attacks to the conjugated position of the enone to yield an enol-enolate. This second step is responsible for the trans relationship at the final cyclopentene. An intramolecular aldolic condensation allows for the formation of the alkoxy cyclopentane intermediate, that by intramolecular nucleophilic attack on the carbonyl group yields a bicyclic ether. The extrusion of the NHC catalys…
Reactions of Alkenes and Alkynes with an Acyclic Silylene and Heavier Tetrylenes under Ambient Conditions
2014
Cycloaddition reactions of the acyclic silylene Si(SAriPr4)2 (AriPr4 = C6H3-2,6(C6H3-2,6-iPr2)2) with a variety of alkenes and alkynes were investigated. Its reactions with the alkynes phenylacetylene and diphenylacetylene and the diene 2,3-dimethyl-1,3-butadiene yielded silacycles (AriPr4S)2tiebar above startSi(CH═tiebar above endCPh) (1), (AriPr4S)2tiebar above startSi(PhC═tiebar above endCPh) (2), and (AriPr4S)2tiebar above startSiCH2CMeCMetiebar above endCH2 (3) at ambient temperature. The compounds were characterized by X-ray crystallography, 1H, 13C, and 29Si NMR spectroscopy, and IR spectroscopy. No reaction was observed with more substituted alkenes such as propene, (Z)-2-butene, te…
Silver ion chromatography and gas chromatography-mass spectrometry in the structural analysis of cyclic dienoic acids formed in frying oils
1995
The nature of the cyclic monoenoic fatty acids formed from linoleic acid in sunflower oil heated to 275°C has been determined by gas chromatography-mass spectrometry of the picolinyl ester derivatives, before and after hydrogenation and deuteration, and following simplification by silver ion high-performance liquid chromatography. In addition, they were examined by gas chromatography-Fourier transform infrared spectroscopy. Cyclopentene fatty acids (50% of the total monoenes) were formed from C-8 to C-12 and C-10 to C-14 of the original chain in equal amounts with unique stereochemistry. In some isomers the double bond appeared to remain in its original position, and in others it migrated t…
The mechanism of ionic diels-alder reactions. A dft study of the oxa-povarov reaction
2014
The mechanism of the oxa-Povarov reaction of a cationic aryl oxonium with cyclopentene and styrene has been studied using DFT methods at the B3LYP/6-31G* level as a reaction model of ionic Diels–Alder (I-DA) reactions. Oxa-Povarov reactions are initialized by an I-DA reaction between the cationic aryl oxonium and alkenes to yield the corresponding formal [4+ + 2] cycloadducts. The last step is a rapid loss of a proton giving chromans. While the I-DA reaction with cyclopentene takes place through a two-stage one-step mechanism, the presence of a phenyl substituent on styrene makes the mechanism of the I-DA reaction stepwise. An electron localization function (ELF) bonding analysis of selecte…
A Synthetic Model for the [4+2] Cycloaddition in the Biosynthesis of the Brevianamides, Paraherquamides, and Related Compounds
2000
Abstract The reactivity of model systems for the proposed [4+2] cycloaddition in the biosynthesis of the brevianamides, paraherquamides, and marcfortines is explored. The model for the intermolecular reaction reveals that the cycloaddition takes place under mild conditions only if activated, very reactive dienophiles are used. When relatively unreactive dienophiles such as cyclopentene and cyclohexene are used, harsh reaction conditions and/or a Lewis acid catalyst are necessary for the reaction. In contrast, the model for the intramolecular reaction demonstrates that the cycloaddition takes place within a few hours at room temperature, even in the absence of a Lewis acid catalyst. Conclusi…
ChemInform Abstract: Palladium-Catalyzed Skeletal Rearrangement of Spirotricyclic Olefins: A Facile One-Pot Strategy for the Synthesis of a Novel Mot…
2013
The first utilization of acyclic cyclopropane bearing spirocyclic olefines for the generation of stereospecific complex fused ring systems with an achiral catalyst is reported.
CCDC 177377: Experimental Crystal Structure Determination
2009
Related Article: H.Detert, D.Lenoir, H.Zipse|2009|Eur.J.Org.Chem.|2009|1181|doi:10.1002/ejoc.200801076
CCDC 894774: Experimental Crystal Structure Determination
2013
Related Article: L.Pilia,E.Sessini,F.Artizzu,M.Yamashita,A.Serpe,K.Kubo,H.Ito, H.Tanaka,S.Kuroda,J.Yamada,P.Deplano,C.J.Gomez-Garcia,M.L.Mercuri|2013|Inorg.Chem.|52|423|doi:10.1021/ic302234j
CCDC 894775: Experimental Crystal Structure Determination
2013
Related Article: L.Pilia,E.Sessini,F.Artizzu,M.Yamashita,A.Serpe,K.Kubo,H.Ito, H.Tanaka,S.Kuroda,J.Yamada,P.Deplano,C.J.Gomez-Garcia,M.L.Mercuri|2013|Inorg.Chem.|52|423|doi:10.1021/ic302234j