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Musolino, Apa, Donato and Pietropaolo 251observed, practically suppressed. The E starting compound is, in fact,thermodynamically more stable than the corresponding Z one.ConclusionsThe main aim of the results concerns the comparison between E and Z isomers, bothtowards hydrogenation and/or isomerization processes. In particular, the less stable Zisomers favor the geometric isomerization products, whereas the most stable (E)-2-buten-1-ol mainly affords a hydrogenated compound. This agrees with earlierfindings, where Z isomers generally favor isomerized (both geometric and doublebond) derivatives (3).When 2-propen-1-ol reacts in the presence of NEt 3 and Rh(I), the reduced sterichindrance and the lack of a possible geometric isomerization are to be expected. So,we explain the large amount of the hydrogenated compound formed (Table 1). In theabsence of NEt 3 , as a rule, hydrogenation of organic substrates generally occurs.However, additionally in this specific case, the reduced reactivity of the systemsuggests that a different catalytic species is operating.Considering all these data, we conclude that the steric hindrance of coordinatedphosphines is the most important factor in determining the behavior of the reactionsstudied.Experimental SectionRhCl(PPh 3 ) 3 was prepared according to the literature (4). The hydrogenation ofdifferent α,β-unsaturated alcohols, 2-propen-1-ol, (E)-2-buten-1-ol, (Z)-2-penten-1-ol,(E)-2-penten-1-ol, (Z)–2-hexen-1-ol, (E)–2-hexen-1-ol, was carried out in liquidphase at 303 K and 0.1 MPa hydrogen pressure, using ethanol as solvent in a batchreactor. A stirring rate of 500 rpm was used. The experimental setup was thoroughlypurged with nitrogen before the beginning of the reaction. The rhodium complex(1.08 x 10 -5 moles) was dissolved, under stirring, in the solvent used (25 mL) inatmosphere of H 2 at 303 K; then, NEt 3 was added in the molar ratio RhCl(PPh 3 ) 3 /NEt 31:100, and the system was allowed to equilibrate for one hour. Finally 15 mL of a 0.6M solution of the α,β-unsaturated alcohol in ethanol, containing an internal standard,was added through one arm of the flask.The progress of the reaction was followed by analyzing a sufficient number ofsamples withdrawn from the reaction mixture. Product analysis was performed with agas chromatograph (Agilent Technologies model 6890N) equipped with a flameionization detector. The product separation was obtained by a capillary column (J&WDB-Waxetr, 50 m, i.d. = 0.32 mm). Quantitative analyses were carried out bycalculating the area of the chromatographic peaks with an electronic integrator.References1. M. G. Musolino, G. Apa, A. Donato and R. Pietropaolo, Catal. Tod; 100, 467(2005).
252Homogeneous Hydrogenation2. R. R. Schrock and J. A. Osborn, J. Am. Chem. Soc.; 98, 2134 (1976).3. M. G. Musolino, P. De Maio, A. Donato and R. Pietropaolo, J. Mol. Catal.: AChem.; 208, 219 (2004).4. J. A. Osborn, F. H. Jardine, J. F. Young and G. Wilkinson, J. Chem. Soc. A; 1711(1966).
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Catalysis ofOrganic Reactions
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14. Catalyst Manufacture: Laborator
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62. Catalysis of Organic Reactions,
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108. Metal Oxides: Chemistry and Ap
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xiii14. The Transformation of Light
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xviien Catalisis y Petroquimica (UN
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xxiiiChronology of Organic Reaction
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To Zsuzsanna and Tim
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Jones et al. 31. On the Use of Immo
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Jones et al. 5three-phase tests in
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Jones et al. 7In the HKR of rac-epi
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Moses et al. 15perrhenate, followed
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Moses et al. 17SnCOSnMe 4≡SiOReO
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Moses et al. 19(AlOSi) of the cube.
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Moses et al. 212.510 3 k obs / s -1
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Wang et al. 233. Catalytic Hydrogen
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Wang et al. 25The rate expressions
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32Halophosphite LigandsIn 1970, Pru
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38Halophosphite Ligands3. P. W. N.
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56Hydrotalcite-like Catalysts[A n-
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58Hydrotalcite-like Catalystssample
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68Synthesis of MIBKwe examined the
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70Synthesis of MIBK1412Conversion (
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72Synthesis of MIBK4,4’-dimethyl
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74Synthesis of MIBKobtained for MIB
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Ardizzi et al. 7710. The Control of
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Ardizzi et al. 79type acidity at th
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84Phenol Benzoylationconsecutive Fr
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86Phenol BenzoylationThis does not
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92Oxidation with Microchannel Immob
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100 Propylene Partial OxidationThe
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102 Propylene Partial OxidationSiO
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104 Propylene Partial Oxidation0.01
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106 Propylene Partial Oxidation0.02
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108 Propylene Partial OxidationRefe
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110Oxidation of n-Pentanemethacryli
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112Oxidation of n-PentaneFReqox1ox2
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114Oxidation of n-Pentanethe presen
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116Oxidation of n-PentaneIn the mec
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118Oxidation of n-PentaneReferences
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120TEMPO Oxidation of Alcoholsthe u
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122TEMPO Oxidation of AlcoholsThe r
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124TEMPO Oxidation of Alcoholsany d
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126TEMPO Oxidation of Alcoholsconce
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128TEMPO Oxidation of AlcoholsMNT :
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130TEMPO Oxidation of Alcoholsuptak
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132Aminoalcohols to Aminocarboxylic
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150CO Oxidation0.02(a)21802110(b)21
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152CO Oxidationcarboxylate species
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Yamauchi 15519. 2006 Murray Raney A
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Yamauchi 157transformation is schem
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Yamauchi 159The X-ray diffraction p
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168Nitrobenzene Hydrogenationfurthe
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170Nitrobenzene Hydrogenationhydrog
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176Nitrobenzene Hydrogenation10. G.
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178 Hydrogenation of Dehydrolinaloo
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304 Catalyst Library DesignIn gas p
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306 Catalyst Library Designd−(b 0
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322 Dendrimer TemplatesThe 100 cm -
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328Rearrangement of 3,4-Epoxy-1-But
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348Heteropoly AcidsSOOO O+ +OS1 2 3
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418 Production of Biodieselto a mas
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422 Production of Biodiesel10080Sel
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448Propylene Oxidation to POSupercr
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450Propylene Oxidation to POTable 1
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464 Chiral 2-Amino-1-Phenylethanolp
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466 Chiral 2-Amino-1-PhenylethanolI
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468 Chiral 2-Amino-1-Phenylethanola
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470 t-Butanol DehydrationResults an
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502 Electroreductive Catalytic Ullm
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504 Electroreductive Catalytic Ullm
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Catalysis of Organic Reactions 507A
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Catalysis of Organic Reactions 509K
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Catalysis of Organic Reactions 511T
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514 Keyword Indexcarboncarbon dioxi
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516 Keyword Indexethanolamine 16 13
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518 Keyword IndexNi, activated 25 2
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520 Keyword Indexsuccinimido ketone
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