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  • Chemistry  (23)
  • Lunar and Planetary Exploration  (5)
  • 1995-1999  (28)
  • 1
    Electronic Resource
    Electronic Resource
    Stereoselective Reactions of Phthalimido-Substituted Radicals Derived from (±)-Threonine: A comparison with reactions of N-phthaloyliminium ions (1998)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 81 (1998), S. 268-284 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Stereoselective reactions of phthalimido-substituted radicals derived from (±)-threonine with different radical traps are reported (Scheme 3, Table 1). A strong influence of the nature of the radical trap on the stereoselectivity was noticed. Small nucleophilic radical traps gave preferentially the syn products. The observed selectivities are explained with the A1,3 strain model and depend on steric and electronic effects (Fig. 2). Reactions with electrophilic radical traps such as diphenyl diselenide gave the anti diastereoisomers with moderate stereocontrol, presumably due to stereoelectronic effects. The same stereochemical outcome, i.e., preferential formation of the anti products, was observed for the reactions of the related N-phthaloyliminium ion (Scheme 5, Table 2). The stereochemistry of the ionic reaction is rationalized by a Felkin-Anh model (Fig. 3).
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19980810208
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  • 2
    Electronic Resource
    Electronic Resource
    Intramolecular Dynamics of Tetranuclear Iridium Carbonyl Cluster Compounds part VIPart V: [1] Derivatives with Bidentate Ligands, Crystal Structures of tetrahedro- Decacarbonyl{μ-[1,1-bis(methylthio-χS)ethane]}tetrairidium ([Ir4(CO)10-(μ2-(MeS)2CHMe)]), tetrahedro-Tri-μ-carbonylheptacarbonyl{μ-{ethylidenebis- [diphenylphosphine]-χP:χP'}}tetrairidium ([Ir4(CO)10(μ2-(Ph2P)2CHMe)]), and tetrahedro-Tri-μ-carbonylheptacarbonyl{μ-{propane-1,3-diylbis[diphenylphosphine]-χP:χP'}}tetrairidium ([Ir4(CO)10(μ2-Ph2P(CH2)3PPh2)]) (1998)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 81 (1998), S. 781-791 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The disubstituted clusters[Ir4(CO)10(μ2-L—L)] with one edge-bridging ligand have a ground-state geometry with all COs terminal (L—L = (MeS)2CHMe, cluster 1) or with three edge-bridging COs (L—L = (Ph2P)2CHMe, cluste 2; L—L =Ph2P(CH2)3PPh2, cluster 3) in the solid state and in solution. A comparative 13C-NMR study of 1-3 shows that their respective ground-state geometries are merely relative minima of energy in the same kinetic profile of successive fluxional processes consisting of a merry-go-round of six COs about a unique trangular face and the rotation of terminal COs about one Ir-atom. The factors affecting the activation energy of the merry-go-round result from the relative bites of the bidentate ligands in the ground-state geometry, as shown by a comparison of the molecular structures of 2 and 3.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19980810328
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  • 3
    Electronic Resource
    Electronic Resource
    The Diels-Alder Reactivity of 2,2′-Ethylidenebis[3,5-dimethylfuran] and Exploratory Chemistry of the Mono-adducts (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1415-1427 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In the presence of Me3Al, 1-cyanovinyl acetate added to 2,2′-ethylidenebis[3,5-dimethylfuran] (1) to give a 20:10:1:1 mixture of mono-adducts 4,5,6, and 7 resulting from the same regiocontrol (‘para’ orienting effect of the 5-methyl substituent in 1). The additions of a second equiv. of dienophile to 4-7 were very slow reactions. The major mono-adducts 4 (solid) and 5 (liquid) have 2-exo-carbonitrile groups. The molecular structure of 4(1RS,1′RS,2SR,4SR)-2-exo-cyano-4-[1-(3,5-dimethylfuran-2-yl)ethyl-7-oxabicyclo[2.2.1]hept-5-en-2-endo-yl acetate) was determined by X-ray single-crystal radiocrystallography. Mono-adducts 4 and 5 were saponified into the corresponding 7-oxanorbornenones 8 and 9 which were converted with high stereoselectivity into (1RS,1′SR,4RS,5RS,6RS)-4-[1-(3,5-dimethyl furan-2-yl)ethyl]-6-exo-methoxy-1,5-endo-dimethyl-7-oxabicyclo [2.2.1]heptan-2-one dimethyl acetal (12) and its (1′RS-stereoisomer 12a, respectively. Acetal hydrolysis of 12a followed by treatment with (t-Bu)Me2SiOSO2CF3 led to silylation and pinacol rearrangement with the formation of (1RS,1′RS,5RS,6RS)-4-[(tert-butyl)dimethy lsilyloxy]-1-(3,5-dimethylfuran-2-yl)ethyl]-5-methoxy-6-methyl-3-methylidene- 2-oxabicyclo[2.2.1]heptane (16). In the presence of Me3Al, dimethyl acetylenedicarboxylate added to 12 giving a major adduct 19 which was hydroborated and oxidized into (1RS,1′RS,2″RS,3″RS,4SR,4″RS,5 SR,6SR)-dimethyl 5-exo-hydroxy-4,6-endo-dimethyl-1-[1-(3-exo,5,5-trimeth oxy-2-endo,4-dimethyl-7-oxabicyclo[2.2.1]hept-2-yl)ethyl]-7-oxabicyclo [2.2.1]hept-2-ene-2,3-dicarboxylate (20). Acetylation of alcohol 20 followed by C=C bond cleavage afforded (1′RS,1″SR,2RS,2′″SR,3RS, 3″SR,4RS,4″SR,5RS)-dimethyl {3-acetoxy-2,3,4,5-tetrahydro-2,4-dimethyl-5-[1-(3-exo,5,5-trimethoxy -2-endo,4-dimethyl-7-oxabicyclo[2.2.1]hept-1-yl)-ethyl]furan-2,5-diyl} bis[glyoxylate] (24).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790514
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  • 4
    Electronic Resource
    Electronic Resource
    Hetero-Diels-Alder Additions of α,β-Unsaturated-Acyl Cyanides. Part 3Part 1: [7], part 2: [8].. Syntheses of 3-bromo-2-ethoxy-3,4-dihydro-2H-pyran-6-carbonitriles, and about their transformation to 2-ethoxy-2H-pyrans (1995)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 78 (1995), S. 151-164 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cycloadditions of the α,β-unsaturated-acyl cyanides 1-3 with (Z)-or (E)-1-bromo-2-ethoxyethene (4) may be performed at moderate temperatures and provide in good yields the 3-bromo-2-ethoxy-3,4-dihydro-2H-pyran-6-carbonitriles 5-7, respectively (Scheme 1). Diastereoisomeric pairs of products result at room temperature merely from the ‘endo’- and ‘exo’-transition states; more complex mixtures appear above 60° as a consequence of (Z)/(E)-isomerization of 4. The relative stability of the anomers of 5 and 6 is explored by treatment with BF3·Et2O. Acid alcoholysis (MeOH or EtOH) of 5 leads to acetals 9a, b of 4-bromo-5-oxopentanoate. Alkyl (2Z,4E)-5-ethoxypenta-2,4-dienoates 12, 17, and 20, are formed in alcoholic alkoxide solutions from 5, 6, and 7, respectively, which is compatible with the intermediacy of 2-alkoxy-2H-pyrans and their valence tautomers, α,β-unsaturatedacyl cyanides. Methoxide addition to the CN group competes with dehydrobromination in case of 5; it leads to 3-bromo-3,4-dihydro-2H-pyran-6-carboximidate 13 (ca. 50% at -20°) which can be hydrolyzed to the methyl carboxylate 14. DBU (1,8-diazabicyclo[5,4,0]undec-7-ene) in benzene converts 5 to 6-ethoxy-2-oxohexa-3,5-dienenitrile (11), the ring-opening product of an obviously unstable 2-ethoxy-2H-pyran; the same reagent dehydrobrominates 6 to 2-ethoxy-4-methyl-2H-pyran-6-carbonitrile (15). HBr Elimination from 7 takes place with great ease in presence of pyridine, or even during chromatography on alumina, and leads to the stable ethyl 6-cyano-2-ethoxy-2H-pyran-4-carboxylate (18); this dimerizes at room temperature to give a 1:3 mixture of tricyclic adducts ‘endo’-21 and ‘exo’-21. The structure of the latter is established by an X-ray crystallographic analysis.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19950780115
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  • 5
    Electronic Resource
    Electronic Resource
    NMR of Enaminones. Part 7Part 6: [l]. The general name enaminone is used for compounds containing the O=C—C=C—N moiety. 1H-, 13C-, and 17O-NMR and X-ray structure determinations of 1,2-disubstituted conjugated 3-[(tert-Butyl)amino]enones (1997)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 80 (1997), S. 2137-2147 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1H-, 13C-, and 17O-NMR spectra for the 2-substituted enaminones MeC(O)C(Me)=CHNH(t-Bu) (1), EtC(O)C(Me)=CHNH(t-Bu) (2), PhC(O)C(Me)=CHNH(t-Bu) (3), and MeC(O)C(Me)=CHNH(t-Bu) (4) are reported. These data show that 3 exists mainly in the (E)-form, 4 in (Z)-form, and 1 and 2 as mixtures of both forms. Polar solvents favour the (E)-form. The (Z)- and (E)-forms exist in the 1,2-syn,3,N-anti and 1,2-anti,1,N-anti conformations A and B, respectively. The structures of the (E)- and (Z)-form are confirmed by X-ray crystal-structure determinations of 3 and 4. The shielding of the carbonyl O-atom in the 17O-NMR spectrum by intramolecular H-bonding (ΔλHB) ranging from -28 to -41 ppm, depends on the substituents at C(l) and C(2). Crystals of 3 at 90 K are monoclinic. with a = 9.618(2) Å, b = 15.792(3) Å, c = 16.705(3) Å, and β = 94.44(3)°, and the space group is P21/c with Z = 8 (refinement to R = 0.0701 on 3387 independent reflections). Crystals of 4 at 101 K are monoclinic, with a = 16.625(8) Å, b = 8.637(6) Å, c = 11.024(7) Å, and β = 101.60(5)°, and the space group is Cc with Z = 4 (refinement to R = 0.0595 on 2106 independent reflections).
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    URL: http://dx.doi.org/10.1002/hlca.19970800713
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  • 6
    Electronic Resource
    Electronic Resource
    Monodentate and Bridging Coordination of 3,3′-Annelated 2,2′-Bipyridines in Zerovalent Palladium- and Platinum-p-quinone Complexes (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 319-330 
    Details
    ISSN: 1434-1948
    Keywords: Palladium ; Platinum ; Bidentate nitrogen ligands ; p-Quinone ; Alkenes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Compounds of the type M(N∩N-κN)(nq)2 and M2(μ2-N∩N)(μ2-pbq)2, in which nq = 1,4-naphthoquinone, pbq = 1,4-benzoquinone, and N∩N is a monodentate or bridging ligand of the α-diimine type, were obtained from reactions of Pd(dba)2 in toluene with the 3,3′-annelated-2,2′-bipyridines: 4,5-diazafluoren-9-one (dafo) and 4,5-diazafluorene (dafe) in the presence of the appropriate p-quinone. In the corresponding reactions with 2,2′-bipyridine (bpy), 1,10-phenanthroline (phen), 2,2′-bipyrimidine (bpym), N,N′-dicyclohexyl-1,4-diaza-1,3-butadiene (chex-dab), bis[N-(o,o′-diisopropyl)phenylimino]acenaphthene (o,o′-iPr2-bian) and 5,6-dihydro-1,10-phenanthroline (dh-phen) only complexes of the type M(N∩N-κ2N)(Q) were formed (Q = nq, pbq). The structures of the complexes have been established by NMR in solution and by X-ray diffraction in the solid state; crystal structures of Pd(bpy-κ2N)(η2-pbq) (1) Pd(dafo-κN)(η2-nq)2 (14) and Pd2(μ2-dafo)(μ2,η2:η2-pbq)2 (16) have been determined. Of the ligands, dafo and dafe are the only ones apt to form complexes containing a monodentate or bridging N∩N ligand. This behaviour is ascribed to the geometrical constraints of dafo and dafe; the annelation by one carbon atom at the 3,3′-positions in these ligands causes an increase in bite angle from approximately 77° to 82°.
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of Chiral Rhenium Complexes Containing Functionalized Thiolate Ligands (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 2055-2061 
    Details
    ISSN: 1434-1948
    Keywords: N-Acetylcysteine ; Amino acids ; Captopril ; Rhenium ; S ligands ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiral racemic rhenium thiolate complexes [CpRe(NO)(PPh3)(SR)] were obtained under either acidic or basic conditions. Thus, when [CpRe(NO)(PPh3)(CH3)] (1) was treated with etheral HBF4 and HSR the thiolate complexes [CpRe(NO)(PPh3)(SR)] [SR = SCH2(2-furyl) (2), SCH2C(O)OEt (3)] were obtained after chromatographic workup. Ligand exchange reactions between [CpRe(NO)(PPh3)(OC4H8)]BF4 (4) and sodium thiolates yielded analogous complexes with SR = SH (5), SCH2CH2Ph (6), SCH2CH=CH2 (7). SR groups which tolerate strongly alkaline conditions may be introduced by treatment of 4 with HSR in the presence of sodium ethoxide as demonstrated by the high-yield synthesis of 2 as well as of complexes with SR = SCH2CH2NHAc (8), SCH2CH2C(O)OH (9). A milder synthesis using hydrated sodium carbonate as a base provided 8 and compounds with SR = SCH2CH2C(O)OMe (10), SCH2CH2C(O)NHCH2Ph (11) in high yields. Using similar methods, thiolate complexes of (R)-N-acetylcysteine (13), its methyl ester (14), (R)-N-phthaloylcysteine (16), and N-[(S)-3-mercapto-2-methylpropionyl]-S-proline (Captopril) (17) were obtained as diastereomeric pairs. The formation of 13 was preceded by the O-bonded isomer 12 which slowly rearranges in solution. 13 can be converted under acidic conditions into its methyl (14) or ethyl (15) esters. The diastereomers of 16 were separated by crystallization, and the structure of the (R,R)-isomer 16a determined.
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  • 8
    Electronic Resource
    Electronic Resource
    C-C Coupling Reactions of (Sulfene)ruthenium Complexes with Enolates (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 605-611 
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    ISSN: 1434-1948
    Keywords: Enolates ; Nucleophilic additions ; Ruthenium ; S ligands ; Sulfenes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Sulfene complexes [CpRu(PR′3)2(RHC=SO2)]PF6 (2a-d) are obtained from the corresponding sulfur dioxide complexes 1a-c and diazomethane or -ethane. Reaction of [CpRu(dppm)(SO2)]Cl (1d) and phenyldiazomethane gives the chlorobenzylsulfinato complex [CpRu(dppm)(SO2CHPhCl)] (3). Alternatively, 2a may be synthesized by sulfur dioxide addition to the carbene complex [CpRu(dppm)(CH2)]PF6 (5) which, in turn, is obtained from the corresponding methyl complex [CpRu(dppm)(CH3)] and [Ph3C]PF6. Treatment of 2a-d or 3 with the enolates of cyclic 2-methyl-1,3-diketones, methyl malonates, open-chain cyano or β-oxo esters, and cyclic β-oxo esters gives the C-C coupling products 6a, b, 7a-e, 8a-c, 9a-c in high yields and, in one case, with high diastereoselectivity as well. The functionalized sulfinate ligands thus formed may be alkylated and subsequently removed from the metal center by ligand substitution with acetonitrile. After MeCN/SO2 exchange, the ruthenium complex can be recycled.
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  • 9
    Electronic Resource
    Electronic Resource
    Chiral Rhenium Complexes of Functionalized Thioaldehydes (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 1435-1443 
    Details
    ISSN: 1434-1948
    Keywords: Captopril ; Cysteine ; Rhenium ; S ligands ; Thioaldehydes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiral racemic rhenium thioaldehyde complexes [CpRe(NO)(PPh3)(η2-S=CHR)]PF6 (2a-g) bearing functionalized aliphatic groups R [R = CH2Ph (a), COOEt (b), CH2COOMe (c), CH2C(O)NHCH2Ph (d), (R)-CH(NC8H4O2)COOMe (e), (S,S)-CH(Me)C(O)NC4H7COOMe (f), C4H3O (g)] have been obtained by hydride abstraction from the corresponding thiolate complexes [CpRe(NO)(PPh3)(SCH2R)] (1a-g). With the exception of 2b, only single stereoisomers with like configurations at rhenium and the thioaldehyde carbon atom were obtained. In some cases, the corresponding sulfinate complexes [CpRe(NO)(PPh3)(SO2CH2R)] (3d-f) were formed as by-products. The analogous toluenesulfinate complex [CpRe(NO)(PPh3){SO2(4-C6H4CH3)}] (3a) has been prepared from [CpRe(NO)(PPh3)(THF)]BF4 (8), and the structure of 3e has been determined by X-ray crystallography. The use of phosphorus ligands other than PPh3 was briefly explored with the synthesis of [CpRe(NO)(PR′3)(η2-S=CHR)]PF6 (5a-d) [R′ = OPh, R = Ph (a), 4-C6H4Cl (b), R′ = iPr, R = Ph (c), H (d)]. Nucleophilic addition of NaSMe to [CpRe(NO)(PPh3){η2-S=CH(4-C6H4OMe)}]PF6 (5e) gave the dithioacetal complex [CpRe(NO)(PPh3){SCH(SMe)(4-C6H4OMe)}] (9) in high yield and with low diastereoselectivity. Diels-Alder additions of 5a, e with 2,3-dimethylbutadiene and 2,3-dimethoxy-butadiene gave complexes of cyclic thioethers (10a-c). From the relative rates of reaction (5a 〉〉 5e) and the low diastereoselectivity, it was concluded that the cycloadditions as well as the nucleophilic addition proceed via the linkage isomers [CpRe(NO)(PR′3)(η1-S=CHR)]PF6.
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  • 10
    Electronic Resource
    Electronic Resource
    Enantioselective Organic Syntheses Using Chiral Transition Metal Complexes, 9 Atropo-Diastereoselective Ring Opening of Biaryl Thionolactones Using [CpRu{(S,S)-CHIRAPHOS}]+ as a Chiral Auxiliary (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 1745-1756 
    Details
    ISSN: 1434-1948
    Keywords: Biaryls ; Lactones ; Nucleophilic additions ; Ruthenium ; S ligands ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The substitution-labile thiophene complex [CpRu{(S,S)-CHIRAPHOS}(SC4H4)]BF4 (2) [(S,S)-CHIRAPHOS = (2S,3S)bis(diphenylphosphanyl)butane], prepared from [CpRu{(S,S)-CHIRAPHOS}Cl] (1), thiophene, and AgBF4, reacted with the biaryl-thionolactones 3a-f to give the corresponding S-coordinated complexes 4a-f in high yields. The structure of 4c, which crystallized as the pure (S,S,P) diastereoisomer, was determined by X-ray crystallography. Coordination of the ruthenium fragment caused an elongation of the C=S bond, a contraction of the C-O bond within the lactone ring and a flattening of that ring. Single hydride transfer with LiBEt3H converted 4a-f into the thiolactolate complexes 5a-f in good yields and diastereoselectivities. An X-ray structure determination of the major isomer of 5a revealed it to be the (S,S,S,P) diastereoisomer. Protonation with NH4PF6 converted 5a-f into the corresponding ring-opened thioaldehyde complexes 6a-f. Alkylation of 5a with methyl iodide resulted in Ru-S cleavage to give the oxothioacetal 7a and [CpRu{(S,S)-CHIRAPHOS}I] (8). Full reduction of 4a-f with LiAlH4 produced the thiolate complexes 9a-f in high yields and 6-74% de. Methylation at sulfur converted 9a-c into the corresponding thioether complexes 10a-c, which were cleaved to 8 and the free methyl thioethers 11a-c without isomerization of the biaryl axis.
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