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Graphical Abstract Angew. Chem. Int. Ed. 432006

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The following Communications have been judged by at least two referees to be “very
important papers” and will be published online at soon:
B. V. Popp, J. E. Wendlandt, C. R. Landis,* S. S. Stahl*
Reaction of Molecular Oxygen with an NHC-Coordinated Pd0
Complex: Computational Insights and Experimental
F. Camerel, R. Ziessel,* B. Donnio, C. Bourgogne, D. Guillon,
M. Schmutz, C. Iacovita, Jean-P. Bucher
Formation of Gels and Liquid Crystals Induced by Pt · · · Pt
Interactions in Luminescent s-Alkynyl Platinum(II) Terpyridine
R. Martinez, R. Chevalier, S. Darses,* Jean-P. Genet*
A Versatile Ruthenium Catalyst for C–C Bond Formation through
C–H Bond Activation
R. Matsubara, S. Kobayashi*
Catalytic Asymmetric Amination of Enecarbamates
H. Nuss, M. Jansen*
Cs5([12]crown-4)2(O3)5 : The First Supramolecular Ozonide
Compound Containing 1¥{Cs8(O3)10}2 Rods
N. Borho, Y. Xu*
Lock-and-Key Principle on a Microscopic Scale: The Case of the
Propylene Oxide · Ethanol Complex
Web Sites
Organic Chemistry Online … and for Free?
A. B. Machotta, M. Oestreich
Organic Light-Emitting Devices
Klaus M$llen, Ullrich Scherf
reviewed by C.-S. Hsu
The Nanotech Pioneers
Steven A. Edwards
reviewed by V. Balzani
Strained Molecules
J. Clayden,* W. J. Moran
No longer left to the imagination: Nonplanar amides have intrigued chemists for
decades. This year, a story 60 years in the
making came to an end: 2-quinuclidone
has finally been synthesized and isolated
in the form of its HBF4 salt (see scheme).
7118 – 7120
The Twisted Amide 2-Quinuclidone:
60 Years in the Making
NMR Spectroscopy
F. C. Schroeder,*
M. Gronquist
7122 – 7131
Extending the Scope of NMR
Spectroscopy with Microcoil Probes
… and to cap it off: Capillary NMR
(CapNMR) spectroscopy is emerging as a
major breakthrough in increasing the
mass-sensitivity of NMR spectroscopic
analysis. As discussed in the Minireview,
not only is the acquisition of the spectra of
mass-limited samples getting easier but
the quality of CapNMR spectra obtained
in many small-molecule applications
exceeds what can be accomplished with
conventional probe designs.
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
Well-orchestrated sequences of events:
The virtues of cascade reactions are the
focus of this Review, which discusses a
number of recent total syntheses that
feature these processes, highlights developments in the field, and points to its
promising future.
Natural Product Synthesis
K. C. Nicolaou,* D. J. Edmonds,
P. G. Bulger
7134 – 7186
Cascade Reactions in Total Synthesis
Mass Spectrometry
Images of the masses: Two-dimensional
molecular imaging of intact rat brain
tissue under ambient conditions was
achieved by using the mass spectrometric
technique of desorption electrospray
ionization (DESI). The distributions of
specific lipids, such as sulfatide 24:1,
reveal distinctive subanatomical features
of the rat brain (cc = corpus callosum;
aca = anterior part of anterior commissure) with spatial resolution of less than
500 mm.
J. M. Wiseman, D. R. Ifa, Q. Song,
R. G. Cooks*
7188 – 7192
Tissue Imaging at Atmospheric Pressure
Using Desorption Electrospray Ionization
(DESI) Mass Spectrometry
Spin Crossover
Room to expand: A rare example of
thermal spin crossover in a MnIII complex
is accompanied by elongation of the
bonds to the equatorial N4 donor set upon
warming (see scheme; Mn purple, N blue,
O red), which is consistent with population of the dx2 y2 orbital. The spin crossover was observed for an N4(O )2 donor
set with axial oxygen donors, whereas only
a temperature-independent high-spin
state was observed with these donors in a
cis arrangement.
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Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
G. G. Morgan,* K. D. Murnaghan,
H. M$ller-Bunz, V. McKee,
C. J. Harding
7192 – 7195
A Manganese(III) Complex That Exhibits
Spin Crossover Triggered by Geometric
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sales tax.
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J.-K. Kim, E. Lee, M. Lee*
7195 – 7198
Nanofibers with Tunable Stiffness from
Self-Assembly of an Amphiphilic Wedge–
Coil Molecule
Thin end of the wedge: A block molecule,
which consists of a rigid wedge-shaped
aromatic segment linked at its apex to a
flexible poly(ethylene oxide) chain, selfassembles into cylindrical nanofibers in
both polar and nonpolar solvents. The
structure of the nanofibers changes
reversibly in response to solvent polarity,
from highly flexible coil-like cylinders in
water to stiff rodlike aggregates in nhexane (see picture).
Knocking them into shape: The total
synthesis of two reported marine natural
products containing halogenated pyrano[3,2-b]pyrans (see example in blue) has led
to the reassignment of both structures as
halogenated 2,2’-bifuranyls (red). Concomitantly an efficient route to pyrano[3,2-b]pyrans is described.
Total Synthesis
Seeing red: Highly sensitive and selective
chemical sensing systems were developed
for the naked-eye detection of toxic ions by
the direct and indirect postgrafting of
hydrophilic and hydrophobic chromophores into spherically nanosized cavities
of cubic Fm3m monoliths (HOM-C10).
This leads to reliable control over the
visual detection of toxic metals such as
PbII, CdII, SbIII, and HgII ions at a low
concentrations ( 10 9 m). DZ = diphenylthiocarbazone.
Environmental Chemistry
H. M. Sheldrake, C. Jamieson,
J. W. Burton*
7199 – 7202
The Changing Faces of Halogenated
Marine Natural Products: Total Synthesis
of the Reported Structures of Elatenyne
and an Enyne from Laurencia majuscula
T. Balaji, S. A. El-Safty,* H. Matsunaga,
T. Hanaoka, F. Mizukami
7202 – 7208
Optical Sensors Based on Nanostructured
Cage Materials for the Detection of Toxic
Metal Ions
Right to the core: A ruthenium(I) complex
of corannulene, prepared in a solvent-free
environment, exhibits two coordination
modes of the bowl: h2-rim and h1-hub (see
picture for the hub-coordinated complex;
Ru purple, O red, C gray, H white). The
latter represents the first example of a
transition-metal center binding only to the
fullerene-like interior of an open geodesic
Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
Polyarene Coordination
M. A. Petrukhina,* Y. Sevryugina,
A. Y. Rogachev, E. A. Jackson,
L. T. Scott
7208 – 7210
Corannulene “Hub” Carbon Coordination
by [Ru2{O2C(3,5-CF3)2C6H3}2(CO)5]
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
It’s all in the mix: A mixed-surfactanttemplated synthesis gives noncrystalline
metal–boron nanotubes (see picture:
TEM image of Fe–B nanotubes; inset: the
corresponding selected-area electron diffraction pattern) from simple starting
materials under mild conditions. These
nanotubes show better catalytic activity
for the hydrogenation of m-nitrotoluene to
m-toluidine than the corresponding
Metal–Boron Nanotubes
Y. Zhu, F. Liu, W. Ding,* X. Guo,*
Y. Chen
7211 – 7214
Noncrystalline Metal–Boron Nanotubes:
Synthesis, Characterization, and CatalyticHydrogenation Properties
Mixed-Valence Compounds
D. Kawakami, M. Yamashita,*
S. Matsunaga, S. Takaishi, T. Kajiwara,
H. Miyasaka, K. Sugiura, H. Matsuzaki,
H. Okamoto, Y. Wakabayashi,
H. Sawa
7214 – 7217
Halogen-Bridged PtII/PtIV Mixed-Valence
Ladder Compounds
Chutes and … Ladders in coordination
networks represent a boundary between
1D and 2D systems. Halogen-bridged PtII/
PtIV mixed-valence ladder compounds
have been synthesized for the first time. In
these compounds, the band gap is controlled by changing the bridging halide
ions. Moreover, by changing counteranions, the charge arrangements of the
ladder compounds can be controlled.
Organic Reactions in Water
Y. Gu, C. Ogawa, J. Kobayashi, Y. Mori,
S. Kobayashi*
7217 – 7220
A Heterogeneous Silica-Supported
Scandium/Ionic Liquid Catalyst System
for Organic Reactions in Water
K. Salaita, Y. Wang, J. Fragala, R. A. Vega,
C. Liu, C. A. Mirkin*
7220 – 7223
Massively Parallel Dip–Pen
Nanolithography with 55 000-Pen
Two-Dimensional Arrays
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Several carbon–carbon bond-forming
reactions are catalyzed by a silica-supported scandium triflate catalyst combined with an ionic liquid. The combination of these two components creates a
hydrophobic reaction environment in
water (see scheme; blue: water, yellow:
substrate, orange: ionic liquid).
Lots of writing on the wall: A simple and
flexible approach for performing highthroughput, large-area, direct-write molecular patterning, without tip feedback, is
demonstrated by using a 55 000-pen twodimensional array of atomic force microscope (AFM) cantilevers. The use of lowaspect-ratio pyramidal tips, curved cantilevers, and a novel gravity-driven alignment method allows parallel patterning of
molecules across 1-cm2 substrate areas at
sub-100-nm resolution.
Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
DNA Structures
Rewriting the end: Two unmodified oligodeoxyribonucleotides (ODNs) were
photochemically ligated through modification of ODNs that contain photosensitive nucleosides at both terminal ends in
the presence of a template ODN. Additionally, this method was applied to the
synthesis of R-shaped DNA as a unique
M. Ogino, K. Fujimoto*
7223 – 7226
Photochemical Synthesis of R-Shaped
DNA toward DNA Recombination and
Processing In Vitro
Controlling guests: Porous coordination
polymers containing mobile organic
groups, such as naphthalene rings (see
picture), are synthesized, and their rotational motion is characterized by solidstate 2H NMR spectroscopy. The rotation
of the groups can be switched off (blue) by
guest (blue spheres) adsorption and
switched on (yellow) again by guest
Metal–Organic Frameworks
S. Horike, R. Matsuda, D. Tanaka,
S. Matsubara, M. Mizuno, K. Endo,
S. Kitagawa*
7226 – 7230
Dynamic Motion of Building Blocks in
Porous Coordination Polymers
Asymmetric Catalysis
E. L. Carswell, M. L. Snapper,*
A. H. Hoveyda*
7230 – 7233
A Highly Efficient and Practical Method
for Catalytic Asymmetric Vinylogous
Mannich (AVM) Reactions
Very selective but very easy: These are two
of the attributes of the asymmetric vinylogous Mannich reactions presented
herein. These reactions can be run on a
gram scale and in undistilled THF and air
Uranyl interactions: The title compound is
the first example of an actinide compound
that contains three different actinyl-ion
coordination geometries, namely, octahedral, pentagonal bipyramidal, and hexagonal bipyramidal. Strong cation–cation
interactions between the uranyl ions lead
to pentamers with a rather unusual configuration (see picture; U dark gray,
O light gray).
Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
(see scheme; TMS = SiMe3). All that is
needed is commercially available AgOAc,
a readily available amino acid derived
phosphine, and a commercially available
or easily prepared (one step) siloxyfuran.
Actinide Chemistry
E. V. Alekseev, S. V. Krivovichev,*
W. Depmeier, O. I. Siidra, K. Knorr,
E. V. Suleimanov,
E. V. Chuprunov
7233 – 7235
Na2Li8[(UO2)11O12(WO5)2]: Three Different
Uranyl-Ion Coordination Geometries and
Cation–Cation Interactions
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Total Synthesis
A. DSmling,* B. Beck, U. Eichelberger,
S. Sakamuri, S. Menon, Q.-Z. Chen, Y. Lu,
L. A. Wessjohann*
7235 – 7239
Total Synthesis of Tubulysin U and V
Multicomponent method: Tubulysins are
among the most potent cytotoxic agents
known. Now the first total synthesis of
some members has been achieved by
utilizing a rapid three-component reaction
for the synthesis of the unusual central
thiazole amino acid tubuvaline (see
scheme; Boc = tert-butoxycarbonyl,
Ac = acetyl), thereby opening new perspectives for anticancer drug development.
Crystal Growth
N. KrSger,* M. B. Dickerson, G. Ahmad,
Y. Cai, M. S. Haluska, K. H. Sandhage,
N. Poulsen, V. C. Sheppard 7239 – 7243
Bioenabled Synthesis of Rutile (TiO2) at
Ambient Temperature and Neutral pH
Biomineral-forming organisms provide
inspiration for developing new reaction
pathways to functional materials, such as
rutile for optical devices. A recombinant
protein (rSilC) was designed based on the
sequence of a silica-forming protein from
a diatom. This unique protein induced the
formation of hierarchically nanostructured
rutile microcrystals under mild reaction
conditions (see SEM image).
An open and closed case: Estradiol was
conjugated to a PAMAM dendrimer (gray
circle) through a short (17a-phenylethynyl) or a long (hexaethyleneglycol) tether
to evaluate how ligand access to a
receptor is affected. With the short tether
(a), the hormone is free and solvent
exposed, with unimpeded access to the
estrogen receptor, while the long tether
(b) wraps around the hormone and the
dendrimer and markedly reduces access
to the receptor.
S. H. Kim,
J. A. Katzenellenbogen*
7243 – 7248
Hormone–PAMAM Dendrimer
Conjugates: Polymer Dynamics and
Tether Structure Affect Ligand Access to
R. M. Hiney, L. J. Higham,*
H. M$ller-Bunz,
D. G. Gilheany*
7248 – 7251
Taming a Functional Group: Creating
Air-Stable, Chiral Primary Phosphanes
No rings of fire! Enantiopure primary
phosphanes have been developed which
are remarkably stable to air oxidation in
both solid and solution states (see example). This new class of stable ligand
synthon appears to owe its stability to
conjugation in their aryl backbones with
the extended p ring system. Even one
extra ring is good enough.
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
Gas-Phase Ionic Liquids
Steaming ahead: The nonvolatility of ionic
liquids is challenged further. Imidazolium(Im)-based ionic liquids composed of
supramolecular structures in the condensed phase (see scheme) vaporize at
ambient pressure from heated (100–
600 8C) solvent droplets as neutral clusters of the type ImnAn.
B. A. DaSilveira Neto, L. S. Santos,
F. M. Nachtigall, M. N. Eberlin,*
J. Dupont*
7251 – 7254
On the Species Involved in the
Vaporization of Imidazolium Ionic Liquids
in a Steam-Distillation-Like Process
A Metal-Catching Linker
An active link: A diglycine-containing
linker (cat·linker) was fabricated on Rink
amide resin for dual functions: a) attachment of a scaffold and b) capture of metal
ions for promoting on-resin reactions (see
picture). The metal-catching feature of the
linker proves essential for the solid-phase
synthesis of indoles through microwaveassisted CuII-mediated heteroannulation.
L.-P. Sun, W.-M. Dai*
7255 – 7258
An Engineered Linker Capable of
Promoting On-Resin Reactions for
Microwave-Assisted Solid-Phase Organic
J. de Vicente, J. R. Huckins,
S. D. Rychnovsky*
7258 – 7262
Synthesis of the C31–C67 Fragment of
Amphidinol 3
A tetrahydropyran intermediate, prepared
from ( )-diethyl tartrate, was used to
assemble the C31–C67 fragment of
amphidinol 3. Both of the tetrahydropyran
rings in the natural product were prepared
from this intermediate. The polyene segment was assembled with high selectivity.
An additional azidomethyl group dramatically decreases the melting points of the
corresponding azidopyrimidines. Theoretical calculations show that these polyazido compounds (see picture; N light
blue, C dark blue, H white) exhibit highly
promising energetic properties. 2,4,6Triazidopyrimidine was found to be a
novel precursor to carbon nanotubes in
the presence of Ni(ClO4)2.
Elusive intermediate trapped: g-Substituted difluoropropargyl groups can stabilize
an organoindium(III) complex. The
resulting structure is the only known
example of an indium atom bonded to a
propargylic carbon atom (see picture;
F blue, S yellow, C white, H green). Reactions with electrophiles produced a
difluoroalkyne or -allene, depending on
the type of electrophile.
Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
Polyazido Compounds
C. Ye, H. Gao, J. A. Boatz, G. W. Drake,
B. Twamley, J. M. Shreeve* 7262 – 7265
Polyazidopyrimidines: High-Energy
Compounds and Precursors to Carbon
Organoindium Reagents
B. Xu, M. S. Mashuta,
G. B. Hammond*
7265 – 7267
Crystallographic Characterization of
Difluoropropargyl Indium Bromide, a
Reactive Fluoroorganometallic Reagent
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Negative-Valent Transition Metals
W. W. Brennessel, V. G. Young, Jr.,
J. E. Ellis*
7268 – 7271
Towards Homoleptic
Naphthalenemetalates of the Later
Transition Metals: Isolation and
Characterization of
Naphthalenecobaltates(1 )
Phosphine Polymers
K. J. T. Noonan,
D. P. Gates*
7271 – 7274
Ambient-Temperature Living Anionic
Polymerization of Phosphaalkenes:
Homopolymers and Block Copolymers
with Controlled Chain Lengths
Taming of the wild anions: Highly labile
naphthalene complexes of formally negative-valent later transition metals have
been obtained in the form of [Co(h4C10H8)(h4-cod)] (see picture; cod = 1,5cyclooctadiene) and [Co(h4-C10H8)2] . The
latter is the first structurally authenticated
homoleptic bis(naphthalene)metal anion
for any d-block element and promises to
be a particularly reactive synthon for the
“naked” atomic cobalt anion.
New kid on the block: Unprecedented
polystyrene-block-poly(methylenephosphine) copolymers are accessible from
the reaction of living polystyrene with the
phosphaalkene (see scheme; Mes = 2,4,6Me3C6H2). The living anionic polymerization of P=C bonds represents a new
development in phosphorus chemistry
and opens up the possibility to synthesize
functional phosphorus polymers of controlled architectures.
Polycarbonate Synthesis
K. Nakano, T. Kamada,
K. Nozaki*
Sidestepping a cyclic side product: Copolymerization of terminal epoxides
with CO2 was investigated by using a
cobalt(III) complex bearing a piperidinium end-capping arm and a piperidinyl
arm (see scheme; DME = 1,2-dimethoxyethane). The catalyst system can selectively produce copolymers without contaminant formation of cyclic carbonates
even at high conversion of the epoxide
(> 99 %).
7274 – 7277
Selective Formation of Polycarbonate over
Cyclic Carbonate: Copolymerization of
Epoxides with Carbon Dioxide Catalyzed
by a Cobalt(III) Complex with a
Piperidinium End-Capping Arm
Surface Chemistry
K. Zhu, J. Hu, C. K$bel,
R. Richards*
7277 – 7281
Efficient Preparation and Catalytic Activity
of MgO(111) Nanosheets
Preferential growth of MgO(111)
nanosheets with a thickness typically
between 3 and 5 nm (see TEM image) has
been achieved by a simple, efficient, and
inexpensive wet chemical route. The
MgO(111) nanosheets have been shown
to have ultrahigh activity for the Claisen–
Schmidt condensation of benzaldehyde
and acetophenone.
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
Xe NMR in Biochemistry
D. Baumer, E. Brunner,* P. Bl$mler,
P. P. ZVnker, H. W. Spiess* 7282 – 7284
Go with the flow: In many applications of
NMR spectroscopy in chemistry, proper
sample preparation is absolutely critical
for success, in particular in biochemical
and biomedical areas. For the NMR
spectroscopy of laser-polarized 129Xe, an
Inequivalent in the crystal: The three
chemically distinct calculated proton
shielding tensors of solid benzene—a
consequence of interactions in the crystal—can be described as the superposition of the isolated molecule and the
intermolecular shielding contributions. In
the ovaloid representations of the shielding tensors 1, 2, and 3 indicate the least,
intermediate, and most shielded principal
axes, respectively.
Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
efficient and robust method for continuous flow of the gas to a NMR tube was
developed. Applications to H2O, DMSO,
phospholipid bicelles, and 2D exchange
NMR spectroscopy are demonstrated.
NMR Spectroscopy of Laser-Polarized
Xe Under Continuous Flow: A Method
To Study Aqueous Solutions of
The tin salt Sn(NTf2)4 (Tf = trifluoromethanesulfonyl) is an efficient catalyst for
the selective and ring-size-specific cycloisomerization of highly substituted 1,6dienes to give six-membered-ring carbocycles (see scheme; X = C(CO2Et)2,
C(CO2Me)2 C(CN)(CO2Et), etc.). This is
the first Lewis acid catalyzed cycloisomerization of this type of substrate.
Cyclohexane Derivatives
An elegant method for the aqueous-phase
hydroformylation of 1-octene with a watersoluble Rh catalyst and amphiphilic latex
particles as phase-transfer agents has
been developed (see scheme). In this way,
substantial concentrations of the olefin in
the aqueous catalyst-containing phase
were reached, and thus reasonable turnover frequencies under mild reaction
conditions could be achieved.
Homogeneous Catalysis
F. Grau, A. Heumann,*
E. DuWach*
7285 – 7289
Cycloisomerization of 1,6-Dienes
Mediated by Lewis Super Acids without
Additives: Easy Access to Polysubstituted
Six-Membered Carbocycles
K. Kunna, C. M$ller, J. Loos,
D. Vogt*
7289 – 7292
Aqueous-Phase Hydroformylation of
1-Octene: Styrene Latices as PhaseTransfer Agents
Shielding Tensors of Benzene
T. Heine,* C. Corminboeuf, G. Grossmann,
U. Haeberlen
7292 – 7295
Proton Magnetic Shielding Tensors in
Benzene—From the Individual Molecule
to the Crystal
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Building bridges: The wheels of [3]rotaxane were intramolecularly tethered to yield
the first member of cyclochiral, interlocked architectures named “bonnanes”
(after the city Bonn, Germany; see
scheme). The enantiomers and meso form
were separated on an immobilized chiral
phase and characterized.
M. Radha Kishan, A. Parham,
F. Schelhase, A. Yoneva, G. Silva, X. Chen,
Y. Okamoto, F. VSgtle*
7296 – 7299
Bridging Rotaxanes’ Wheels—Cyclochiral
Supporting information available on the WWW
(see article for access details).
A video clip is available as Supporting Information
on the WWW (see article for access details).
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2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 7102 – 7112
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