chemistry letters · pdf filec-28 chemistry letters vol.33, ... in the photo-fries...

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Chemistry Letters http://www.csj.jp/journals/chem-lett/ Vol.33 No.3 CMLTAG March, 2004 ISSN 0366-7022 Copyright Ó 2004 The Chemical Society of Japan 206 Enantiomeric Resolution of Intramolecular Amine–Borane Complex with a Chiral Boron Center B NMe 2 Ph O * B NMe 2 O Ph * (S) O C 2 F 5 O C 2 F 5 racemization G 116 kJ mol –1 at 83 °C (R) Shinji Toyota, Tomohiro Hakamata, Naoya Nitta, and Fumiko Ito 208 Synthesis of Novel Nano-structured Clays: Unique Conformation of Pillar Complexes Rh + ClO 4 - N N H 2n+1 C n H 2n+1 C n Clay n = 1-23 Norihito Yamaguchi, Shogo Shimazu, Nobuyuki Ichikuni, and Takayoshi Uematsu 210 The First Luminescent Anionic Bis(ethynyl- phenanthroline)gold(I) Complex N N Au N N N N Au Au Ph 3 P PPh 3 - Green Luminescent Complexes Youhei Yamamoto, Michito Shiotsuka, Sigeru Okuno, and Satoru Onaka 212 Selection of RNA-binding Peptides Contain- ing an Arg-rich Motif observed m/z Mass / m/z a b c d a: 2993.4 b: 3008.5 c: 3050.6 d: 3064.8 20 40 60 80 100 120 2800 2900 3000 3100 3200 3300 3400 %Intensity 0 Naohiko Shimada, Reiko Iwase, Tetsuji Yamaoka, and Akira Murakami

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Page 1: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

Chemistry Lettershttp://www.csj.jp/journals/chem-lett/

Vol.33 No.3 CMLTAGMarch, 2004 ISSN 0366-7022

Copyright � 2004 The Chemical Society of Japan

206 Enantiomeric Resolution of IntramolecularAmine–Borane Complex with a ChiralBoron Center

B

NMe2

PhO

* B

NMe2

O

Ph

*

(S)O

C2F5

O

C2F5

racemization

∆G≠ 116 kJ mol–1

at 83 °C (R)

Shinji Toyota, Tomohiro Hakamata, NaoyaNitta, and Fumiko Ito

208 Synthesis of Novel Nano-structured Clays:Unique Conformation of Pillar Complexes

Rh+ ClO4-

N

N

H2n+1Cn

H2n+1Cn

Clay

n = 1-23

Norihito Yamaguchi, Shogo Shimazu,Nobuyuki Ichikuni, and Takayoshi Uematsu

210 The First Luminescent Anionic Bis(ethynyl-phenanthroline)gold(I) Complex

N NAu

N N

N NAuAuPh3P PPh3

-

Green Luminescent Complexes

Youhei Yamamoto, Michito Shiotsuka, SigeruOkuno, and Satoru Onaka

212 Selection of RNA-binding Peptides Contain-ing an Arg-rich Motif observed m/z

Mass / m/z

ab

c

d

a: 2993.4

b: 3008.5

c: 3050.6

d: 3064.8

20

40

60

80

100

120

2800 2900 3000 3100 3200 3300 3400

%In

tens

ity

0

Naohiko Shimada, Reiko Iwase, TetsujiYamaoka, and Akira Murakami

Page 2: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

C-28 Chemistry Letters Vol.33, No.3 (2004)

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

214 Direct Observation of the Liþ–18-Crown-6Complex Working as H2O Capture in Ace-tone–Water Mixture

Yoichi Kikuchi, Kayoko Haramoto, ShunsukeMochizuki, and Akihiro Wakisaka

216 Self-organized Nanocomposites of Function-alized Gold Nanoparticles with Octa(3-ami-nopropyl)octasilsesquioxane

Si O Si

O

Si

O

Si O

Si

O

O

OSi O

OSi

O

OOSi NH3

+-OOC

NH3+

NH3+

NH3+

+H3N

+H3N

+H3N

+H3N

S

S

S

S

COO-

S

SS

S

-OOC

Au AuCOO-

Xiaqin Wang, Kensuke Naka, Hideaki Itoh, andYoshiki Chujo

218 Topographical Imaging of Soft Structures ofLipid Membranes at Water–solid Interfaceby Fluorescence Interferometry

The schematic illustration of an experimentalsystem under a fluorescence microscopeKenji Suzuki and Hiroshi Masuhara

220 Lattice Deformation of Strain-induced Crys-tallites in Carbon-filled Natural Rubber The degree of lattice deformation of

the natural rubber crystallites becamesmaller by filling with carbon black.This result implies that as some localstress was transferred to carbon black,relatively less stress was apportionedto strain-induced crystallites.

0.955

0.960

0.965

0.970

0.975

0.980

0.985

0 10 15Stress / MPa

volu

me

/ nm

3

NR-0

NR-20H

NR-40H

5Sirilux Poompradub, Masatoshi Tosaka, ShinzoKohjiya, Yuko Ikeda, Shigeyuki Toki, IgorsSics, and Benjamin S. Hsiao

222 Electroless Formation of Pressure SensitiveThin Films of Platinum Porphyrin UsingSurfactants with an Azobenzene Group

0.0

0.2

0.4

0.6

0.8

1.0

1.2

0.0 0.2 0.4 0.6 0.8 1.0P / Pref

I ref /

I

Substrate: ITO: stainless

∆: Ni(styrene-co-methyl methacrylate)

Stern−Volmer plot:Iref/I = A + B (P/Pref)

octaethylporphyrin and poly-Stern−Volmer plot for platinum

films. Pref: 100 kPa, Tref: 293 K.

Yoshitaka Ito, Kazunori Mitsuo, Keisuke Asai,Ichiro Okura, and Tetsuo Saji

Page 3: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

Chemistry Letters Vol.33, No.3 (2004) C-29

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

224 Synthesis of Graft Copolymer from Polysil-sesquioxane Initiated by Photoiniferter

Si

O

Si

O

O

Si

Si

O

n

SiO

Si

O

O

Si

Si

O

n

CH2SCNEt2

S

CH2 CH2 CH SCNEt2

C Om

S

NMe2H2C CH

C

O

NMe2

hν,

Osamu Moriya, Shin-ichi Yamamoto, TakeoKumon, Toshifumi Kageyama, Atsuko Kimura,and Toshio Sugizaki

226 Intermolecular Communication on LipidBilayer Membrane. Control of EnzymaticActivity Triggered by a Lipid Signal

Specific activation of a lipid signalswitched on an enzyme action throughsystematic and multiple molecularrecognitions on lipid bilayer membrane.

EnzymeSignal

activator

Lipid signalLipid bilayer

Wen-Jie Tian, Yoshihiro Sasaki, Atsushi Ikeda,Jun-ichi Kikuchi, and Sheng-Di Fan

228 CdS Nanobelts on Si Substrate

Weifeng Liu, Chuangui Jin, Chong Jia,Lianzeng Yao, Weili Cai, and Xiaoguang Li

230 A Novel 3-D Network of Fe(II) Gglutarate: 2-D Honeycomb-type Edge-shared FeO6

Layers and Isolated Interlayer FeO6 Octahe-dra

YooJin Kim, YunJu Park, Duk-Young Jung,Sangjun Oh, Dae Sung Kim, and Jung Chul Sur

232 Curdlan and Schizophyllan (�-1,3-Glucans)can Entrap Single-wall Carbon Nanotubesin Their Helical Superstructure

500 nm

β-1,3-Glucan - SWNT

Munenori Numata, Masayoshi Asai, KenjiKaneko, Teruaki Hasegawa, Norifumi Fujita,Yumiko Kitada, Kazuo Sakurai, and SeijiShinkai

Page 4: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

C-30 Chemistry Letters Vol.33, No.3 (2004)

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

234 Synthesis of Novel Luminescent Substratesand Their Incorporation into a Protein Onlyat a Terminal Site via a Transglutaminase-catalyzed Enzymatic Reaction

proteinTb3+

P KP

Q F MQ

transglutaminase

Tb 3+

Masumi Taki and Kazunari Taira

236 New Synthesis of Isoquinoline Derivatives byReactions of 2-(2-Methoxyethenyl)benzoni-triles with Organolithiums and Lithium Di-alkylamides

Kazuhiro Kobayashi, Taiyo Shiokawa, OsamuMorikawa, and Hisatoshi Konishi

238 Synthesis of SF2809-V, Chymase Inhibitor,and Its Analogs by Three Component Reac-tion: Model Study for High Throughput Syn-thesis of a Chymase Inhibitor Library

A

OH B

CHO

HN

C A

OH HN

B

C

+ +AcOH

OO

Yasuo Yamamoto and Kenzo Harimaya

240 Cytoplasmic Molecular Delivery by Hemato-porphyrin Derivative-based PhotodynamicTreatment Using High-intensity PulsedLaser Irradiation

Yuuichi Miyamoto, Yoshiaki Suzuki, TakashiMeguro, and Masaya Iwaki

242 Photorefractivity of Mixtures of a Ferroelec-tric Liquid Crystal and Photoconductive Pol-ymers

Interference in FLC

Charge generation

Charge transport

Generation of internalelectric field

-

Change in orientations ofFLC molecules

Yukihito Nakazawa and Takeo Sasaki

Page 5: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

Chemistry Letters Vol.33, No.3 (2004) C-31

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

244 Large Scale Fabrication of Hollow PalladiumNanospheres by Template-free Approach In large-scale and high yields hollow palladium nanospheres were fabricated by template-

free approach in one step at room temperature.

Xuanjun Zhang, Qingrui Zhao, Yupeng Tian,and Yi Xie

246 A Novel Method for the Preparation ofGreen-photoluminescent Zinc Oxide by Mi-crowave-assisted Carbothermal Reduction

Gre

en-P

L in

tens

ity /

a. u

.

35302520151050

Vde

nsity

/ a.

u.

: green-PL

: Vo.

o.

Percentage of carbon reacted / wt%Tetsushi Yamamoto, Yuji Wada, HiromitsuMiyamoto, and Shozo Yanagida

248 Baeyer–Villiger Oxidations in Ionic Liquids.A Facile Conversion of Ketones to Esters andLactones

O

O

ONN

+ m-CPBA

rt

+ BF4-

J. S. Yadav, B. V. S. Reddy, A. K. Basak, andA. V. Narsaiah

250 Highly Isospecific Polymerization of Propyl-ene with Bis(phenoxy-imine) Zr and Hf Com-plexes Using iBu3Al/Ph3CB(C6F5)4 as a Co-catalyst

PPM

23.0 22.0 21.0 20.0 19.0

mmmr mmrrmmrm mrrm

iBu3Al/Ph3CB(C6F5)4

Propylene CH3 CH3 CH3

nN

OHfCl22 mmmm: 96.8 %

Tm: 165.1 °C

Aitha Vishwa Prasad, Haruyuki Makio, JunjiSaito, Mitsuhiko Onda, and Terunori Fujita

252 Direct Alkylation and Phenylation of 3,8-Di-bromo-1,10-phenanthroline with GrignardReagents

NBr Br

NBr Br

RMgX

R = alkyl, phenyl

+

R

N

N

Kazushige Anzai, Hiroki Fukumoto, andTakakazu Yamamoto

Page 6: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

C-32 Chemistry Letters Vol.33, No.3 (2004)

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

254 Isolation of Cyclohexadienone Intermediatesin the Photo-Fries Rearrangement of 2,4-Di-methylnaphth-1-yl and 1,4-Dimethylnaphth-2-yl 2,4,6-Trimethylbenzoates

O

OMes

O OMes

Mes =

O

MesO

Three isomericacylcyclohexanones were isolatedin good yields from thephotolysates of partially or fullyblocked naphthyl esters.

and

Tadashi Mori, Makoto Takamoto, HideakiSaito, Takahiro Furo, Takehiko Wada, andYoshihisa Inoue

256 Remarkable Differences in Photo and Ther-mal (Acid-catalyzed) Reactivities betweenortho- and para-Acylcyclohexadienones asEssential Factors Determining the OverallEfficiency of the Photo-Fries Rearrangement O O

MesO

Mes

O

+

O

OMes

O

MesO

hν (313 nm)

hν (313 nm)No reaction

"Ortho" and"para"-cylcyclohexadienones,prepared photochemically,showed completely differentphotochemical and acid-catalyzedbehavior.

OH

+

Tadashi Mori, Makoto Takamoto, HideakiSaito, Takahiro Furo, Takehiko Wada, andYoshihisa Inoue

258 Amphiphilic Cyclodextrins as Novel Mono-saccharide Transport Carriers through aBulk Liquid Membrane

O

OOH

OH

OSitBuR2

R = Ph, n = 7 R = Me, n = 7R = Ph, n = 8 R = Me, n = 8

n

Monosaccharides, such as D-ribose, D-xylose,and D- glucose, were successfully transportedthrough a bulk liquid membrane by usingamphiphilic β - and γ -cyclodextrin carriers.

Toshiyuki Kida, Takeru Ohe, HiroyukiHigashimoto, Hitoshi Harada, Yohji Nakatsuji,Isao Ikeda, and Mitsuru Akashi

260 Separation of Warfarin Enantiomers byCapillary Gas Chromatography with ChiralStationary Phase Chiral capillary GC of warfarin

enantiomeric pair

Iwao Abe, Daiki Nagamatsu, TaketoshiNakahara, and Gerd Fabian

262 Rapid Crystallization of High Quality CubicSillica SBA-16 Nanoporous Material

(a) (b)

(c) (d)

[100]

[110] [111]

Chi-Feng Cheng, Yi-Chun Lin, Hsu-HsuanCheng, Shr-Miau Liu, and Hwo-Shuenn Sheu

Page 7: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

Chemistry Letters Vol.33, No.3 (2004) C-33

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

264 Direct Speciation of Tin Compounds in Envi-ronmental Samples Using Sn K-edge XANES

29.14 29.20 29.26

Systematic broadening of the first broad peak

Sn K-edge XANES of (Bu)nSnCl4-n

Direct Speciationof Organotin !!

TeBT

MBT

DBT

TBT

SnCl4

Energy (keV)

Rel

ativ

e ab

sorb

ance

Naoki Sakakibara, Yoshio Takahashi,Yoshitaka Yamaguchi, Kiyoshi Shibata, andTomoya Uruga

266 Improved Long-range Order of SiliciousMCM-41 by Gradual Heating of SynthesisGel

A. K. Sinha, S. Seelan, T. Akita, S. Tsubota, andM. Haruta

268 Preparation of TiO2 Photocatalysts byMulti-gelation and Their Photocatalytic Reactivityfor the Degradation of 2-Propanol

(pH swing)

Basic side Acid side

Principle of Multi-Gelation MethodTiO2 (Hydrous) Small particle

Bernaurdshaw Neppolian, Hiromi Yamashita,Yoshimi Okada, Hiroaki Nishijima, andMasakazu Anpo

270 Synthesis of Meso-/Macroporous Zeolite(Fe,Al)-ZSM-5Microspheres from Diatomite

Wei Shan, Yahong Zhang, Yajun Wang,Jianchao Xia, and Yi Tang

272 Self-initiated Chain-growth Polycondensa-tion for Aromatic Polyamides

HN

C8H17

C

O

OPh

N

C8H17

Et3Si

CsF/18-crown-6N

C8H17

C

O

OPhC

O

HN

C8H17Initiatorin situ

NC8H17

CO

OPhH

n

1

: 2

Chain-GrowthPolycondensation

1

Mn < 21000Mw/Mn < 1.1

Tsutomu Yokozawa, Ryuji Sugi, ToshinobuAsai, and Akihiro Yokoyama

Page 8: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

C-34 Chemistry Letters Vol.33, No.3 (2004)

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

274 An Efficient and Green Synthesis of 2-Aryl-benzothiazoles in an Ionic Liquid, [pmIm]Brunder Microwave Irradiation

MW 3-5 min

NH2

SH

N

SRRCHO

[pmIm]Br

Brindaban C. Ranu, Ranjan Jana, and SuvenduS. Dey

276 Synthesis and Properties of 9,90-Diaryl-4,5-diazafluorenes. A New Type of Electron-Transporting and Hole-Blocking Materialin EL Device

NN

MeO

1a

A phosphorescent EL deviceusing 1a as a hole-blocking layerexhibited a maximum externalquantum efficiency of 18%.

OMe

Katsuhiko Ono, Tomoki Yanase, MasakazuOhkita, Katsuhiro Saito, Yosuke Matsushita,Shigeki Naka, Hiroyuki Okada, and HiroyoshiOnnagawa

278 Surface-enhanced Infrared Spectrum of COAdsorbed on Cu Electrodes in Solution

Ge prism

IR radiation

C

O

C

O

C

O

C

OCu thin film

nanoparticles

Vacuumevaporated Cu

Chemicallydeposited Cu

IR spectra of CO

Hiroto Miyake and Masatoshi Osawa

280 Preparation of Hydrogenated Surfactant/SCCO2 Micelles and Their MicropolarityDetermination C12H25(OCH2CH2)5-OH

C6H13(OCH2CH2)5-OHC10H21(OCH2CH2)-OHC10H21(OCH2CH2)5-OH

Zameer Shervani, Juncheng Liu, and YutakaIkushima

282 High Selective Conversion of Poly(ethyleneterephthalate) into Oil Using Ca(OH)2 It is a well-known fact that sublimation

substances, such as benzoic acid and terephthalicacid, are produced in the thermal decompositionof PET, and this causes problems in plasticrecycling plants. However, it is clear that theaddition of Ca(OH)2 affects the high selectivity ofbenzene without producing sublimationsubstances. The yield of benzene was 35.85 wt %at 700 °C and a 10.0 Ca(OH)2/PET molar ratio.This value means that the selectivity of benzeneis 78.8% for liquid products, and 85.1 wt % foraromatic ring in input PET.

Abu

ndan

ce /

Arb

itra

ry U

nit

Ca(OH)2 /PET = 1

0 5 10 15 20 25Retention time / min

Benzene

Toluene Stylene

Indene

Acetophenone

NaphthaleneBenzoic acid

Biphenyl

1,1‘-Methylenebis-benzene

Ca(OH)2 /PET= 3

Ca(OH)2 /PET= 5

Ca(OH)2 /PET =10

Ca(OH)2 /PET = 0

Toshiaki Yoshioka, Eisaku Kitagawa, TadaakiMizoguchi, and Akitsugu Okuwaki

Page 9: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

Chemistry Letters Vol.33, No.3 (2004) C-35

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

284 Electrochemical Behavior of Methyl- andButyl- Terminated Si(111) in Aqueous Solu-tion

-1.5

-1.1

-0.7

-0.3

0.1

-1.4 -0.9 -0.4 0.1

Potential / V vs. Pt | Fe 2+ / Fe3+

Cur

rent

Den

sity

/ m

A c

m-2

Methyln-ButylH-Si

Daisuke Niwa, Tomoyuki Inoue, HiroshiFukunaga, Toru Akasaka, Taro Yamada,Takayuki Homma, and Tetsuya Osaka

286 Novel Ultrasonication-assisted CarbonylAllylation Mediated by SnCl2 in Water Carbonyl allylation mediated by SnCl2 in water

under ultrasonication without using any Lewisacid catalyst.

Br+

R1

R2

OSnCl2

. 2H2O / Ultrasonication

H2O

OH

R1R2

a b c(60%~90%)

Jun Wang, Gu Yuan, and Chang-Qing Dong

288 Potassium Hydrogen Sulfate-Catalyzed Re-actions of Indoles: AMild, Expedient Synthe-sis of Bis-indolylmethanes

+

OH, rt N

R

HNH

NH

+ RCHOKHSO4

CH3

Electrophilic substitution of indole with aldehydes catalyzedby potassium hydrogen sulfate is reported.

Rajagopal Nagarajan and Paramasivan T.Perumal

290 Synthesis and Characterization of StrontiumCarbonate Nanowires with a Axis Orienta-tion and Dendritic Nanocrystals

The strontium carbonate nanowires that growalong the a axis were synthesized in largescale through simple hydrothermal approachfor the first time. The aspect ratio of theproduct is more than 1000. Dendriticnanocrystals were also generated at lowtemperatures. Moreover, this method isfeasible to be applied in the synthesis ofbarium carbonate nanowires.

Qing Huang, Lian Gao, Ye Cai, and FritzAldinger

292 Water Sorption of CaCl2-ContainingMateri-als as Heat Storage Media

CaCl2

Heat

H2OHeat storage capacitywith water sorption onCaCl2/FSM16 was 3.5times as high as that onNa form Y-zeolite.

Chun Yi Liu, Kentaro Morofuji, Kenji Tamura,and Ken-ichi Aika

Page 10: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

C-36 Chemistry Letters Vol.33, No.3 (2004)

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

294 Palladium-Catalyzed H–D Exchange Reac-tion under Hydrothermal Condition

Seijiro Matsubara, Yutaka Yokota, andKoichiro Oshima

296 Charge Transport in a �-Stacked Poly(di-benzofulvene) Film

hole drift through stacked π-electron system

Tamaki Nakano, Tohru Yade, MasaakiYokoyama, and Norio Nagayama

298 Effects of K5SiW11O39Co on MitogenicActivity of Basic Fibroblast Growth Factor Conformation changes of bFGF

induced by POM (K5SiW11O39Co) were observed by fluorescence andCD spectra. The mitogenic assayshowed that POM in variousconcentration ranges produceddifferent effects on mitogenic activityof bFGF.

Liwei Sun, Qiang Wu, Ning Liu, Cheng Yang,Liyan Liu, Zhiqiang Liu, and Daqing Zhao

300 Monophosphate as Eminent Ligand to BindCe(IV)/EDTA Complex for Site-selectiveDNA Hydrolysis

O P

O

O-

O-OP

O-O

O-

Ce(IV)/EDTA

Highly selective DNA scission

Substrate DNA

Wen Chen, Tomoyuki Igawa, Jun Sumaoka,and Makoto Komiyama

302 Carbon–Carbon Bond Formation in GlycolicAcid Generated Spontaneously from Di-chloromethane in Hot Water

CH2(OH)2 + HCOOH HOCH2COOH + H2O(C1) (C1) (Glycolic acid; C2)

A new carbon−carbon bond formation in hot water was found.

Hydrothermal reaction of dichloromethane (CH2Cl2) at 1 mol/dm3

leads to the formation of glycolic acid at an yield of 50% withoutmetal catalysts in the temperature range of 200−250 °C.

Chihiro Wakai, Saiko Morooka, NobuyukiMatubayasi, and Masaru Nakahara

Page 11: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

Chemistry Letters Vol.33, No.3 (2004) C-37

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

304 Bi(OTf)3- and Bi(TFA)3-Catalyzed RingOpening of Epoxides with Anilines underMicrowave Irradiation

R2+ NH2

OR2 NHCH2CHR1

OHR1

R2 NHCHCH2OH

R1

orBi(OTf)3 or Bi(TFA)3

MW/CH3CN20−195 s 75−96%

Ahmad R. Khosropour, Mohammad M.Khodaei, and Kazem Ghozati

306 Stereoselective Intercalation of Hexose forLayered Double Hydroxide by Calcination–Rehydration Reaction

Sumio Aisawa, Hidetoshi Hirahara, SatoshiTakahashi, Yoshio Umetsu, and Eiichi Narita

308 First Example of a Heptacyclic Tetranuclear,Five- and Six-coordinate Titanium Complex,[{(iPrO)2Ti(�3-O)TiCl(iPrO)((OC6H4)2PPh)g2]

Synthesis and structural characterization of a novel tetranuclear titanium complexcontaining bis(o-phenol)phenylphosphine is described. The structure is a rareexample with titanium having four different types of oxygen bindings.

Srinivasan Priya, Maravanji S. Balakrishna, andJoel T. Mague

310 The Sea Urchin-shaped CaCO3 via TemplateMineralization on Surface-functionalizedVaterite Particles by Tiopronin-protectedGold Nanoparticles

Tiopronin-Protected

Gold Nanoparticles

CaCl2 +(NH 4)2CO3Vaterite

Dong-Ki Keum, Kensuke Naka, and YoshikiChujo

312 Iron(III) Chloride as a Water-CompatibleLewis Acid for Diastereoselective Aldol Re-actions in Water in the Presence of a Surfac-tant

+Ph

OSiMe3

Ph Ph

OFeCl3 (10 mol %)

PhCHO

OHC12H25C6H4SO3Na (10 mol %)

H2O, 0 °C, 12 h

89% yieldsyn/anti = 91/9

Naohiro Aoyama, Kei Manabe, and ShuKobayashi

Page 12: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

C-38 Chemistry Letters Vol.33, No.3 (2004)

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

314 A Facile Synthesis of Various Fluorine-Con-taining Indole Derivatives via Palladium-Catalyzed Annulation of Internal Alkynes

Rf R

NH2

I+

NH

Rf

R

NH

R

Rf+

Pd(PPh3)4, (20 mol%)Et3N (1.0 equiv.)

DMF, 80 °C

Major MinorRf = CF3, CHF2

R = aryl, alkylJungha Chae, Tsutomu Konno, TakashiIshihara, and Hiroki Yamanaka

316 A Reaction Intermediate Involved in Oxy-genation of Catecholatoiron(III) Complexeswith Molecular Oxygen — Relevance to Cat-echol Dioxygenases

400 600 800 10000

1

2

Wavelength / nm

ε / m

M–1

cm–1

A: Fe(III)–Cat Complex

B: O2–bound intermediate

+ O2– O2

A

B

Yutaka Hitomi, Yuichiro Tase, MasakazuHiguchi, Tsunehiro Tanaka, and TakuzoFunabiki

318 New Fluorescent Stains for Protein Detectionin Sodium Dodecyl Sulfate–PolyacrylamideGels

N

R

H3C

N

S

NR

H3C

N

Se

N

R

H3C

N

O

R = C15H31

++

+

0

10

20

30

40

Flu

ores

cenc

e In

tens

ity (

a.u.

)0 10 15

4

6

8

10

12

T ime (nanoseconds)

400 500 600 700 800

with SDS

with protein

Wavelength (nm)

ln[P

hoto

n C

ount

s, a

.u.]

5

Soo Yeon Hong, Hyunsook Jun, Seung SooYoon, Chulhun Kang, and Myungkoo Suh

320 First Application of Calixarenes as Extract-ants in Room-temperature Ionic Liquids Aqueous phase

Ionic liquid phase

Ag

N

OOO O

N NN

+

Kojiro Shimojo and Masahiro Goto

322 Facile One-pot Syntheses of Amidines andEnamines from Oximes via Beckmann Rear-rangement Using TrifluoromethansulfonicAnhydride

COOMe

COOMeNa

NOH

MePh

PhHN

Me

Et3N

N

Me

OTf

PhNMe Ph

Me

N

N

Ph

Ph

Me

Tf2O

Me

N

COOMe

COOMe

Ph

HMe

NH

COOMe

COOMe

Ph

Tomofumi Takuwa, Tomofumi Minowa, JimYoshitaka Onishi, and Teruaki Mukaiyama

Page 13: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

Chemistry Letters Vol.33, No.3 (2004) C-39

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

324 Direct Chemical Synthesis of Gold Nano-wires with 2-D Network Structure and Rela-tionship between the Presence of Gold Ionsand Shape Stability of Gold Nanowires

Gold nanowires uniformly covering a 2-dimensional space were synthesized bydirect reduction of AuCl4 with sodium-

citrate. The shape stability of nanowireswas related to the presence of gold ions inthe solution phase.

Lihua Pei, Koichi Mori, and Motonari Adachi

326 Excited-state Intramolecular Proton Trans-fer (ESIPT)-type Phosphorescence of 2-Ami-nobenzophenone in 77K Matrices

Excited triplet state of photoenol (3Enol*) of 2-aminobenzophenone(2-ABP) in 77 K matrices has been observed by laser-induced luminescencespectroscopy.

O 2 OH NH *

1Enol*

1OH NH *3

3Enol*

ESIPT ISC

12-ABP*

*1NH

Masahide Hagiri, Nobuyuki Ichinose,Jun-ichiro Kinugasa, Tatsuya Iwasa, andToshihiro Nakayama

328 Synthesis of Functionalized Fullerene byMono-alkylation of Fullerene Cyclopentadi-enide

K+

RRR

RRR

R

R

FG-R

R = Me, Ph

FG-RX

FG-R =

OH

OEt

O etc.

OR R

Ryo Hamasaki, Yutaka Matsuo, and EiichiNakamura

330 Desulfurization of Thiophene in AlkalineSupercritical Water Studied by 1H and 13CNMR

Thiophene was successfully desulfurized in supercritical water, and was disintegrated into S2- and such carboxylic acids as formic, acetic, and succinic acids.

Shinya Yoshida, Koji Takewaki, Keiichi Miwa,Chihiro Wakai, and Masaru Nakahara

332 Synthesis of L-Cysteine and L-Cysteic Acidby Paired Electrolysis Method L-Cysteine and L-cysteic acid were

synthesized by paired eletrolyesis method.A high purity over 98% and high yieldover 90% of both products were gained.The cyclic voltammetry behaviors ofhydrobromic acid and cystine showed atypical EC catalytic process took place inthe anodic cell. Anode reaction andsuccessive chemical reaction acceleratedeach other to get a high speed and currentefficiency.

Electrode electrolytes were:

anode: 10 Br− − 10e ← 5Br2

electrolyte of anode: 5Br2 + RSSR + 6H2O

2RSO3H + 10H+ + 10Br−

cathode: RSSR+2H+ + 2e 2HOOCH(NH2)CH2SH

R = HOOCH(NH2)CH2−

reaction and chemical reaction in the

Xixin Wang and Jianling Zhao

Page 14: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

C-40 Chemistry Letters Vol.33, No.3 (2004)

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

334 Growth of Sb2O3 Nanotubes via a SimpleSurfactant-assisted Solvothermal Process We report a simple surfactant-assisted

solvothermal synthesis of Sb2O3

nanotubes. The nanotubes have anorthorhombic structure with outerdiameters range from 40 to 150 nm, thewall thickness of 10 to 40 nm and alength of up to several micrometers. Thenanotubes might be formed by a rollingprocess.

Yunxia Zhang, Guanghai Li, and Lide Zhang

336 Synthesis of Bamboo-shaped TiO2 Nano-tubes in Nanochannels of Porous AluminumOxide Membrane

Tianyou Peng, Huanping Yang, Gang Chang,Ke Dai, and Kazuyuki Hirao

338 Physical Properties of MonofluorodimethylCarbonate

Monofluorodimethyl carbonate (MFDMC)exerts the polar effect on physical properties.Relative permittivity (εr), viscosity (η), anddensity ( ) of MFDMC are higher than thoseρof dimethyl carbonate (DMC) over atemperature range of 10 to 70 °C, whereasrefractive index (nD) becomes lower.

MFDMC

C

O

OOCH3CH3

C

O

OOCH2FCH3

DMCMasahiro Takehara, Susumu Watanabe,Noritoshi Nanbu, Makoto Ue, and Yukio Sasaki

340 6-Amino-6-deoxychitosan. Preparation andApplication as Plasmid Vector in COS-1Cells

Taku Satoh, Takeshi Nagasaki, Nobuo Sakairi,and Seiji Shinkai

342 Controlled Assembly of Dinuclear Metallo-rings into 1D Coordination Polymer andMixed-metal Rare Earth Complexes withRed-to-Green Luminescence Properties

Novel rings connected by chains one-dimensional (1D) coordination polymerof rare earth complex have been rationally synthesized by the reaction of Eu(NO3)3

and L, 1,4-bis{[(2’-benzyl aminoformyl)phenoxyl]methyl}benzene.

Three adjacent strands of the 1D coordination polymer (H atomsare omitted for clarity)

Zheng-Hong Cai, Yu Tang, Wei-sheng Liu, andMin-Yu Tan

Page 15: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

Chemistry Letters Vol.33, No.3 (2004) C-41

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

344 Particle Size Control of 11-Mercaptoundeca-noic Acid-Protected Au Nanoparticles byUsing Heat-treatment Method

Kyung-Hoon Kim, Mami Yamada, Dae-WonPark, and Mikio Miyake

346 Spin-coating Preparation of High QualityMesoporous Titania Nanofilms

Ningzhong Bao, Kazumichi Yanagisawa,Xiaohua Lu, and Xin Feng

348 Heck-type Benzylation of Olefins with BenzylTrifluoroacetates

Hirohisa Narahashi, Akio Yamamoto, and IsaoShimizu

350 A Tripodal Ligand Containing Three Imida-zole Groups Inducing Spin Crossover in BothFe(II) and Fe(III) Complexes; Structures andSpin Crossover Behaviors of the Complexes

χ MT

/ cm

3 K

mol

–1

T / K

0 100 200 300

4

3

2

1

Fe(II) complex Fe(III) complex

Hiromi Ohta, Yukinari Sunatsuki, MasaakiKojima, Seiichiro Iijima, Haruo Akashi, andNaohide Matsumoto

352 Water-free Solution Synthesis of Monodis-perse Cu2S Nanocrystals

Cluster CompoundsPure & Monodisperse

NC ArrayFor Optical Device

H2OH2OProcessing

Toshihiro Kuzuya, Saeki Yamamuro, TakehikoHihara, and Kenji Sumiyama

Page 16: Chemistry Letters · PDF fileC-28 Chemistry Letters Vol.33, ... in the Photo-Fries Rearrangement of 2,4-Di- ... 274 An Efficient and Green Synthesis of 2-Aryl

C-42 Chemistry Letters Vol.33, No.3 (2004)

Copyright � 2004 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

354 Novel 1-D Water Nanowires in Crystal of anOrganic Host

Water Nanowire-I Water Nanowire-II

Akio Wakahara and Toshimasa Ishida

356 Light-triggered Luminescence ModulationUsing Labile Axial Coordination to Zinc–Porphyrin

N N

NNZn

N

RN

N

OFF

N N

NNZn

ON

N

RN Nfluorescence

quench

~330 nm

~440 nm

Joe Otsuki, Koichi Narutaki, and Jan M. Bakke

358 Crystal Structure of a Liquid CrystallineFerrocene Derivative, 1,10-bis[10-[4-(4-meth-oxyphenoxycarbonyl)phenoxy]decyloxycar-bonyl]ferrocene

The first example of U-type structure of liquid crystallineferrocene derivatives.

Naotake Nakamura and Takashi Okabe