Condensation of propiolic esters with olefins catalyzed by the C5H5Fe(CO)2 cation

Rosenblum, M.; Scheck, D.

doi:10.1021/om00062a028

Cited by 56 publications

(16 citation statements)

References 1 publication

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“…The observation of only two resonances with coupling constant of 5. 7 Hz in the nonaromatic region of the 1 H NMR spectrum is in agreement with the proposed symmetrical ring structure. The observed number of 13 C NMR signals and the coupling patterns also support the proposed ring-expansion structure.…”

Section: Resultssupporting

confidence: 88%

Nickel-Catalyzed [2+2] Cycloaddition of Alkynes with Activated Cyclic Alkenes: Synthesis and Novel Ring Expansion Studies of Cyclobutene Products

Huang¹,

Rayabarapu²,

Li³

et al. 2000

Chem. Eur. J.

100

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Oxabenzonorbornadienes 1 and 2 and azabenzonorbornadiene 3 undergo [2+2] cycloaddition with alkynes (PhC triple bond Ph, PhC triple bond CMe, PhC triple bond CCO2Et, PhC triple bond CCH(OEt)2, and HC triple bond C(CH2)4Me) in the presence of [Ni(PPh3)2Cl2], PPh3, and Zn powder in toluene to afford the corresponding exo-cyclobutene derivatives 4a-e, 5a-e, and 6 in fair to excellent yields. Under similar conditions. EtCO2C triple bond CCO2Et does not react with 1 in toluene to give the [2+2] cycloaddition product, but in acetonitrile, the catalytic [2+2] cycloaddition proceeds and cycloadduct 4 f is isolated in 83% yield. At high temperature, these cyclobutene derivatives readily undergo ring expansion to yield the corresponding 8-membered carbocyclic dienes. Thus, flash vacuum pyrolysis of 4a, 4d, 4f, 6, and 14 at 500 degrees C affords dienes 13a-d and 15 in 70-96% yields. This interesting ring expansion may be viewed as the insertion of an alkyne moiety into the carbon-carbon double bond of a cyclic olefin resulting in the enlargement of the ring by two carbons. Compound 13a is readily deoxygenated by TiCl4 and Zn in THF to give a cyclooctatetraene derivative 16 in 89% yield.

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Section: Resultssupporting

confidence: 88%

Nickel-Catalyzed [2+2] Cycloaddition of Alkynes with Activated Cyclic Alkenes: Synthesis and Novel Ring Expansion Studies of Cyclobutene Products

Huang¹,

Rayabarapu²,

Li³

et al. 2000

Chem. Eur. J.

100

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“…A particular example is the ethereal complex, [CpFe-(CO) 2 (THF)]BF 4 [34] in which the labile tetrahydrofuran (THF) is coordinated to the metal centre through the oxygen atom. This complex has been proven to be an essential precursor in the synthesis of various cyclopentadienyliron complexes [4,[10][11][12][13][15][16][17][18][19][20]35], as well as catalysts in various organic syntheses such as the [2+2] cycloaddition of alkenes [36], Diels-Alder reactions [37,38], cyclopropanation [27,[31][32][33], epoxidation [29,30] and aziridination [25][26][27][28], among others [3,[22][23][24]27,29,39]. In all these reactions THF is easily displaced by the desired substrate to form either the desired intermediate or desired end product.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of amine complexes of the cyclopentadienyliron dicarbonyl complex cation, [Cp(CO)2Fe]+

M’thiruaine

Friedrich

Changamu

et al. 2011

Inorganica Chimica Acta

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[{CpFe(CO) 2 } 2 l-(NH 2 (CH 2 ) n NH 2 )](BF 4 ) 2 (n = 2-4) (3), respectively. These complexes have been fully characterized and the mass spectral patterns of complexes 2 are reported. The structures of compounds 2a (n = 2) and 2b (n = 3) have been confirmed by single crystal X-ray crystallography. The single crystal X-ray diffraction data show that complex 2a, [CpFe(CO) 2 NH 2 (CH 2 ) 2 CH 3 ]BF 4 , crystallizes in a triclinic P 1 space group while 2b, [CpFe(CO) 2 NH 2 (CH 2 ) 3 CH 3 ]BF 4 , crystallizes in an orthorhombic Pca2 1 space group with two crystallographically independent molecular cations in the asymmetric unit. Furthermore, the reaction of 1 with 1-alkenes gives the g 2 -alkene complexes in high yield.

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“…High temperature and pressure was used to decompose this catalyst poisoning complex (126). Under reaction conditions, an iron carbonyl compound results in the formation of H 2 Fe(CO) 4 , which is considered to be the hydrogenating agent (Scheme 173) (254). With fully hydrogenated product, a mixtures of double-bond isomerized monoenoic fatty esters have been observed with considerable cis-trans isomerization (254).…”

Section: Hydrogenation Of C-c Unsaturated Bondsmentioning

confidence: 99%

Iron Catalysis in Synthetic Chemistry

Rana

Modak

Maity

et al. 2014

Progress in Inorganic Chemistry: Volume 59

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Condensation of propiolic esters with olefins catalyzed by the C5H5Fe(CO)2 cation

Cited by 56 publications

References 1 publication

Nickel-Catalyzed [2+2] Cycloaddition of Alkynes with Activated Cyclic Alkenes: Synthesis and Novel Ring Expansion Studies of Cyclobutene Products

Nickel-Catalyzed [2+2] Cycloaddition of Alkynes with Activated Cyclic Alkenes: Synthesis and Novel Ring Expansion Studies of Cyclobutene Products

Synthesis and characterization of amine complexes of the cyclopentadienyliron dicarbonyl complex cation, [Cp(CO)2Fe]+

Iron Catalysis in Synthetic Chemistry

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