Showing papers on "Norbornadiene published in 1989"
TL;DR: Norbornene and norbornadiene derivatives have been shown to react with aryl and vinyl halides in the presence of a palladium catalyst, formic acid, and tributylamine or piperidine to give hydroarylated and hydrovinylated derivatives in good to high yield as mentioned in this paper.
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TL;DR: In this article, a palladium-catalyzed synthesis of coumarin, involving ring formation from o-iodophenol, norbornadiene, and carbon monoxide, followed by elimination of cyclopentadiene is described.
40 citations
TL;DR: In this article, the NBD ligand in Pt(CF3)2(NBD) has been replaced under mild conditions by a number of neutral S-, N-, and O-donor ligands to form cis-PtCF32L2 complexes.
38 citations
TL;DR: The atropisomeric bis(dialkylarylphosphine) ligands, (R)-(−)- and (S)-(+)-2,2′-bis(dicyclohexylphosphino)-6,6′-dimethyl-1,1′-biphenyl (BICHEP) (1) have been newly synthesized, whose Rh(I) complexes are highly efficient catalysts for asymmetric hydrogenations of ethyl α-(benzamido)cinnamate and dimethyl itaconate in up
Abstract: The atropisomeric bis(dialkylarylphosphine) ligands, (R)-(−)- and (S)-(+)-2,2′-bis(dicyclohexylphosphino)-6,6′-dimethyl-1,1′-biphenyl (BICHEP) (1) have been newly synthesized, whose Rh(I) complexes are highly efficient catalysts for asymmetric hydrogenations of ethyl α-(benzamido)cinnamate and dimethyl itaconate in up to 98% yields and 98–99% enantiomeric excess.
37 citations
TL;DR: La reaction du norbornadiene avec plusieurs derives de l'acetylene, silyles ou non, en presence d'un complexe Co(acac) 3, donne des derives de deltacyclene et de tricycloheptane as mentioned in this paper.
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TL;DR: In this paper, the formation of composes d'inclusion is selective, i.e., the composition of a compositional composition is formed by reaction of β-CD avec aucun complexe (COD) ou (NBD) de metal-transition.
TL;DR: In this article, two sulfur atoms of the different dithiolato ligands are added to one of the double bonds of NBD and the reactions of 1 with quadricyclane (Q) are 103-104 times faster than those with NBD.
TL;DR: P PtCl(diene)R (diene = hexa-1,5-diene (hex) or norbornadiene (nbd), R = C6F5, p-HC6F4, or p-MeOC6F2(dcy)2(nbd) was obtained in high yield from Me3SnR when a 1 2 mole ratio was used as discussed by the authors.
TL;DR: In this article, the crystal structure of tetrameric (cod)Ru( d, l -phe)Cl]4 demonstrates that the amino acidate ligands are tridentate with symmetrical carboxyl bridges between individual Ru atoms.
TL;DR: In this paper, 16 new cationic copper(I) complexes have been synthesized, and characterized by IR and 13C NMR spectroscopy, including cyclohexene and diphenylacetylene.
TL;DR: In this article, a platinum bead electrode was used to demonstrate solvent-dependent e.r.t. spectra implying solvent co-ordination at one axial site for tetrahydrofuran (thf)-CH2Cl2 mixtures at -196 °C.
Abstract: The complexes [Rh2L4{µ-2,3-(NH)2C10H6}][1; L2=(CO)(PPh3) or η4-cod (cyclo-octa-1,5-diene)] and [Rh2L4{µ-1,8-(NH)2C10H6}][2; L2=(CO)(PPh3), η4-cod, η4-nbd (norbornadiene), or η4-tfbb (tetrafluorobenzobarrelene)] undergo two sequential one-electron oxidations at a platinum bead electrode. At –78 °C, the chemical oxidation of compound (1; L2=η4-cod) or (2; L2=η4-cod) in thf, with [CPh3][BF4] in CH2Cl2, gives the [Rh2]3+-containing salts [Rh2(η4-cod)2(η-L1)][BF4][1+; L1= 2,3-(NH)2C10H6 or 2+; L1= 1,8-(NH)2C10H6] which, in tetrahydrofuran (thf)-CH2Cl2 mixtures at –196 °C, show solvent-dependent e.s.r. spectra implying thf co-ordination at one axial site. The irreversible one-electron reduction of [Rh2(NO)(η4-cod)2{µ-1,8-(NH)2C10H6}][PF6](3), prepared from (2;L2=η4-cod) and [NO][PF6] in CH2Cl2, leads to the loss of NO and the regeneration of (2; L2=η4-cod).
TL;DR: In this article, the Fourier transform ion cyclotron resonance (FTICR) mass spectrometer was used to determine the reaction mechanisms and rate constants for the reactions of ions produced from a number of precursors.
Abstract: : The reactions of C5H3+ and C5H5+ ions with acetylene and diacetylene were investigated using a Fourier transform ion cyclotron resonance (FTICR) mass spectrometer. The ejection capabilities of FTICR were used to determine the reaction mechanisms and rate constants for the reactions of ions produced from a number of precursors. While different structures could be attributed to C5H3+ ions produced from different precursors on the basis of reactivity, this could not be done for C5H5+ ions, whose reactivity was similar regardless of precursor. Different percentages of reactive C5H5+ structure(s) were produced from various precursors using several charge transfer gases. Formation of C5H5+ from norbornadiene and cycloheptatriene was studied in more detail and existence of a second formation mechanism was shown to be possible. Results are discussed in relation to previous work involving C3H3+ and C5H5+ reactions and a proposed ionic route to soot formation.
TL;DR: Ni(COD)2/Ph3P or Ni(acac) 2/Et3Al/Ph 3P have been shown to be effective catalysts for the stereoselective homo Diels-Alder reaction between norbornadiene and electron deficient olefins.
TL;DR: In this paper, the stereochemistries of cycloadditions of mesitonitrile oxide to norbornadiene and nine 7-substituted derivatives have been investigated.
TL;DR: Reverse electron-demand Diels-Alder reaction of ethyl 6-(2-thienyl)-1,2,4-triazine-3-carboxylate with norbornadiene in boiling p-xylene followed by the elimination of cyclopentadiene (retro Diels Alder reaction) gave fusaric acid as mentioned in this paper.
Abstract: Reverse electron-demand Diels-Alder reaction of ethyl 6-(2-thienyl)-1,2,4-triazine-3-carboxylate with norbornadiene in boiling p-xylene followed by the elimination of cyclopentadiene (retro Diels-Alder reaction) gave 5-(2-thienyl)pyridine-2-carboxylate. Desulfurization of the thienyl-pyridine with Raney nickel and subsequent saponification afforded fusaric acid (5-butylpyridine-2-carboxylic acid)
TL;DR: The stereochemistry of photocycloaddition reactions of various cyclodienes to hexafluorobenzene in cyclohexane solution depends on the structure of the cyclodiene and [2+2]cycloadducts as discussed by the authors.
Abstract: The stereochemistry of photocycloaddition reactions of various cyclodienes to hexafluorobenzene in cyclohexane solution depends on the structure of the cyclodiene and [2+2]cycloadducts are mainly observed Photoreaction of 1,5-cyclooctadiene with hexafluorobenzene gives nearly equal amounts of syn and anti[2+2]adducts, which are further transformed to tetracyclic systems, contrary to this, the stereochemistry observed by reactions with 1,4-cyclohexadiene depends on the molar ratio of cyclodiene–hexafluorobenzene and 30–54% of syn addition is observed, the syn adduct, however, being further transformed to 2,3,4,5,6,7-hexafluoropentacyclo[64002,703,1106,10]dodec-4-ene Syn selectivity of [2+2]cycloaddition was enhanced when bicyclic dienes were used and it is interesting that in the case of norbornadiene and benzonorbornadiene only exo attack was observed, and no anti attack occurred in the case of benzonorbornene The quantum yields of [2+2]photocycloaddition reactions depend on the structure of the c
TL;DR: In this paper, the homo-Diels-Alder reaction of norbornadiene with internal alkynes was performed with 3-hexyne, 1-phenyl-2-trimethylsilylacetylene and 1-trimsilyl-1.
01 May 1989
TL;DR: In this article, the mechanism of catalytic activity of transition metal complexes is discussed in terms of an effective Hamiltonian of a reactant-catalyst system, and the potential energy surface has been constructed for the reaction of isomerization of quadricyclane to nonbornadiene.
Abstract: The mechanism of the catalytic activity of transition metal complexes is discussed in terms of an effective Hamiltonian of a reactant-catalyst system. The potential energy surface has been constructed for the reaction of catalytic isomerization of quadricyclane to nonbornadiene. The properties of the catalyst are found to affect strongly the activation energy of the reaction.
TL;DR: The usefulness of the reaction between trialkyl(aryl)stannanes and dihalogeno(η 4 -diene)platinum(II) has been tested with regard to the synthesis of sterically hindered (aryl)(halogenon)(η 3,4,5,6)-platinum (II) compounds as discussed by the authors.
TL;DR: In this paper, a number of square-planar rhodium(I) complexes containing 2-quinaldinate (C9NH6COO−) as monoanionic N,O bidentate have been synthesized by means of the reaction.
TL;DR: In this paper, the face-to-face D2h dimer of norbornadiene has been confirmed by the X-ray analysis of a single crystal of the 1,3-bis(methoxycarbonyl) derivative (2), monoclinic, space group C2/c, a= 16.570(6), b= 8.073(4), c= 12.151(4)A, β= 114.89(2)°, final R= 0.055, Rw=0.070.
Abstract: The proposed structure of garudane (1), the face-to-face D2h dimer of norbornadiene, has been confirmed by the X-ray analysis of a single crystal of the 1,3-bis(methoxycarbonyl) derivative (2), monoclinic, space group C2/c, a= 16.570(6), b= 8.073(4), c= 12.151(4)A, β= 114.89(2)°, final R= 0.055, Rw= 0.070. Detailed structural characteristics observed for (2) are compared with the isomeric D2d dimer (isogarudane)(3). Compound (1) is calculated to be 44 kcal mol–1 mere strained than (3). The demethylenation procedure on (1)—and the 1,4-bis homo[7] prismane (10) of similar structure—as a potential synthetic route to [6]- and [7]-prismanes (4) and (5) has advantages over the intramolecular [2 + 2]-photocyclization of polycyclic dienes [e.g.(12) and (13)] and the pinacolic coupling of polycyclic diketones [e.g.(14)]. These are discussed on the basis of strain analysis.
TL;DR: In this article, the intramolecular Diels-Alder reaction of the dichloro-1,2,4-benzotriazine derivatives was also investigated.
Abstract: Ethyl 5,6,7,8-tetrahydro-1,2,4-benzotriazine-3-carboxylate was treated with sulfuryl chloride to give ethyl 5,5,8,8-tetrachloro-5,6,7,8-tetrahydro-1,2,4-benzotriazine-3-carboxylate. Following dehydrochlorination of the tetrachloro compound with triethylamine afforded ethyl 5,8-dichloro-1,2,4-benzotriazine-3-carboxylate. The dichloro-1,2,4-benzotriazine derivative was heated with norbornadiene in p-cymene to give ethyl 5,8-dichloroquinoline-2-carboxylate. Intramolecular Diels-Alder reaction of the dichloro-1,2,4-benzotriazine derivatives was also investigated
TL;DR: In this article, two-to-one (cyclodextrin:guest) inclusion compounds for transition metal complexes of cycloocta-1,5-diene (cod) and norbornadiene (nbd) with cyclodextrins were prepared.
Abstract: Inclusion compounds of transition metal complexes of cycloocta-1,5-diene (cod) and norbornadiene (nbd) with cyclodextrins were prepared. Two-to-one (cyclodextrin:guest) inclusion compounds were obtained in high yields by the treatment of β-cyclodextrin (β-CD) with [(L)RhCl]2 (L = nbd or cod) and 1:1 inclusion compounds were obtained by the reaction of β-CD with (cod)PtX2 (X = Cl, Br, or I) in high yields, while γ-CD formed 1:1 inclusion compounds with (cod)PtX2 (X = Br or I). The formation of inclusion compounds is selective. α-CD did not form inclusion compounds with any transition-metal complexes with cycloocta-1,5-diene. Thermogravimetric measurements show that the complexes are stabilized by inclusion in cyclodextrin cavities. The inclusion compounds were characterized by 1 H-NMR, IR, UV, and circular dichroism spectra.
TL;DR: In this article, the 6-31G* and 6 -31G** SCF levels and the RMP2 level for bicyclo[2.2.5,7-triene and 2.2loctane were calculated.
Abstract: Bbs_tract Ab initio calculations of bicyclo[2.2.2locta2,5,7-triene (barrelenel, bicyclo[2.2.2]octa-2,5-diene, bicyclo[2.2.2loct-2-ene, and bicyclo[2.2.2loctane were performed at the 6-31G* and 6-31G** SCF levels and the 6-31G* RMP2 level. The results for these and model compounds, such as norbornadiene and Dewar benzene, enable comparison with the experimental thermochemistry in the barrelene series and a reassessment of the extent of destabilization in barrelene.
TL;DR: In this article, the effects of the concentrations of base and rhodium complex, and the presence of substituents in the phosphine ligand on the rate and selectivity of the reaction were studied.