bluuebunny/crossref_metadata_2025_split huggingface dataset:
Simultaneous Multielement Determination of Major, Minor, and Trace Elements in Soil and Rock Samples by Inductively Coupled Plasma Emission Spectrometry.
Authors: Tao Hiroaki , Iwata Yasuo , Hasegawa Tetsuya , Nojiri Yukihiro , Haraguchi Hiroki , Fuwa Keiichiro 
Published: July 2006

Abstract
A simple and convenient analytical method for simultaneous multielement determination of soil and rock samples has been investigated by inductively coupled plasma emission spectrometry. Spectral interferences due to major elements were examined in detail, and the correction coefficients for minor and trace elements were estimated for correction of matrix effects. The determinations of minor and trace elements as well as major elements could be performed without matrix matching of the standard solutions. The present method investigated has been applied to the analysis of various soil and rock samples, and the analytical results have been compared with those obtained by atomic absorption spectrometry.
A Cation-exchange Study of the Hydrolysis of Tracer Concentrations of Polonium(IV)
Authors: Suganuma Hideo , Hataye Itsuhachiro , Takashima Yoshimasa 
Published: July 2006

Abstract
A cation-exchange method was used for determining the average cationic charge of polonium species present in hydrolytic equilibrium in solutions. This method is based on measurements of the distribution ratio of polonium at a constant internal hydrogen-ion concentration of the cation-exchanger phase. In 1.0 mol dm−3 (H,Na)ClO4 and 1.0 mol dm−3 (H,Na)NO3 solutions at −log[H+]=1.0, tracer concentrations of polonium(IV) were found to exist in the mean chemical forms of Po(OH)3.430.53+ and Po(OH)2.83(NO3)0.600.57+, respectively. The formation of cationic polymerized species was also estimated in region of 4≤−log[H+] in a 1.0 mol dm−3 (H,Na)ClO4 solution.
The Reductive Coupling of Organic Halide Using Hydrazine and a Palladium Amalgam Catalyst. II. Homocoupling of Haloarene with Arylhydrazine
Authors: Nakajima Riichiro , Kinosada Masaji , Tamura Takashi , Hara Tadashi 
Published: July 2006

Abstract
The function of palladium chloride in the reaction of an arylhydrazine with a haloarene was found to differ from those of other metal salts; palladium chloride was reduced with arylhydrazine, and the palladium metal produced was again oxidized with haloarene to give palladium halide. Thus the reductive coupling of haloarene occurred in the presence of a catalytic amount of palladium chloride. Addition of mercury(II) chloride promoted this reaction. The reaction of o-, m-, and p-bromotoluene with the corresponding tolylhydrazine gave the corresponding bitolyl in 99, 112, and 115% yield, respectively, based on the haloarene.
Sesquiterpenoid Constituents of the Liverwort Frullania brotheri STeph.
Authors: Takeda Reiji , Ohta Yoshimoto , Hirose Yoshio 
Published: July 2006

Abstract
Two new sesquiterpene lactones, (+)-β-frullanolide and (+)-brothenolide, have been isolated from the liverwort Frullania brotheri STeph. One of them, (+)-brothenolide, has an allergenic property. The absolute structures of these lactones have been established by spectroscopic analysis and chemical transformation.
Sesquiterpenoid Constituents of the Liverwort, Ptychanthus striatus (LEhm. et LIndenb.) NEes
Authors: Takeda Reiji , Naoki Hideo , Iwashita Takashi , Mizukawa Kosei , Hirose Yoshio , Isida Toshimasa , Inoue Masatoshi 
Published: July 2006

Abstract
Four sesquiterpenoids, striatene, striatol, β-monocyclonerolidol and ptychanolide, were isolated from the liverwort Ptychanthus striatus (LEhm. et. LIndenb.)NEes. Their structures have been established by spectroscopic analysis and chemical transformation. Three of them, striatene, striatol and β-monocyclonerolidol, are interesting in terms of the evolution of the liverwort from the algae.
CD Spectra and Absolute Configurations of fac(a,b,c)-[Co(a)(b)(c)(1,4,7-Triazacyclononane)]n+ Complexes
Authors: Fujinami Shuhei , Hosokawa Takao , Shibata Muraji 
Published: July 2006

Abstract
Seventeen kinds of fac(a,b,NH3)-[Co(a)(b)(NH3)(tacn)]n+ complexes (a, b=CN−, NO2−, SO32−, NCS−, N3−, CH3COO−, H2O, OH−, Cl−, or Br−; tacn=1,4,7-triazacyclononane) have been prepared and optically resolved by column chromatography. The absolute configurations of these complexes have been determined by referring to the CD spectra of the related [Co(a)(gly)(tacn)]n+ complexes (a=CN−, NO2−, NCS−, N3−, or Cl−). It has been found that the signs of the Cotton peaks observed in the first absorption band region are closely related to the ligand field strengths of the unidentate ligands, and that the dominant Cotton peak is associated with the electronic transition which arises in the plane containing no ammonia molecule.
Syntheses of 5-Deoxy-, 5,4′-Dideoxy-, 5-Deoxy-5-epichloro-, and 5,4′-Dideoxy-5,4′-diepichlorokanamycin A
Authors: Miyake Toshiaki , Tsuchiya Tsutomu , Nishi Toshiyuki , Umezawa Sumio 
Published: July 2006

Abstract
5,4′-Dideoxy-5,4′-diepichlorokanamycin A has been synthesized from 1,3,6′,3″-tetrakis(N-benzyloxycarbonyl)-4″,6″-O-cyclohexylidenekanamycin A by treatment with sulfuryl chloride, followed by deblocking. Similar treatment of 2′,3′,4′,2″-tetra-O-acetyl-1,3,6′,3″-tetrakis(N-benzyloxycarbonyl)-4″,6″-O-cyclohexylidenekanamycin A gave 5-deoxy-5-epichlorokanamycin A. 5,4′-Dideoxykanamycin A and 5-deoxykanamycin A were synthesized from the corresponding 5,4′-diepichloro and 5-epichloro derivatives by reductive dechlorination with sodium metal in liquid ammonia or tributylstannane. The structures of these derivatives were confirmed by the 1H- and 13C-NMR spectroscopy.
Aryliminodimagnesium Reagents. VI. The Reactions with Conjugated Carbonyl Compounds. The Initial Coordination and the Electron-transfer in the Reactions of Organomagnesium Reagents
Authors: Okubo Masao , Yoshida Masatoshi , Horinouchi Kotomi , Nishida Hiroshi , Fukuyama Yoshinori 
Published: July 2006

Abstract
The reactions of aryliminodimagnesium reagents (ArN(MgBr)2) with benzylideneacetophenones, quinones, and benzils were examined. Among the product-distributions in the reactions with the enones and the α-diketones, some examples in which p-MeO-substituted substrates gave higher yields of condensation products were obtained. The results are in contrast with the product-distributions in the reaction of ArMgBr with Ar1COAr2 and that of ArN(MgBr)2 with Ar1NO2: p-Cl-Substituted substrates are advantageous for the formation of addition and/or condensation products. These reactions of the two organomagnesium reagents were classified into “coordination controlled” and “electron-transfer controlled” ones on the basis of the combination of electron-donating ability of reagents with the electron-accepting ability of substrates. The classification was illustrated also on the basis of the relative difference of the energy levels of HOMO’s and LUMO’s of the reactants.
The Mechanism of the Reaction of 3,5-Dinitrobenzonitrile with Sodium Methoxide in Methanol
Authors: Abe Takehiro 
Published: July 2006

Abstract
The reaction of 3,5-dinitrobenzonitrile in a methanolic solution containing a low sodium-methoxide concentration has been reinvestigated. The final product has been found to be methoxy(3,5-dinitrophenyl)methanimine, which is produced by a catalytic reaction. The reaction mechanism has been presented for the formation of the Meisenheimer complexes and the final product in the reaction system. The rate and thermodynamic stabilities for their formation have been discussed on the basis of the LUMO coefficients of 3,5-dinitrobenzonitrile and from the relative potential energies of their formation respectively, considering also the solvent effects.
The Disproportionate Constants of Mercurry(I) in Dilute Solutions. II
Authors: Sanemasa Isao , Kobayashi Toyohisa , Deguchi Toshio , Nagai Hideo 
Published: July 2006

Abstract
The equilibrium constants, Kd, of mercury(I) disproportionation have been measured by passing air containing mercury(0) vapor through mercury(I) solutions. At 15, 20, 25, 30, and 35 °C, the values of Kd were 1.3, 2.9, 5.2, 8.8, and 11×10−9 mol dm−3 respectively at μ=0.1 (NaClO4).
The Isotope Effects in the Reactions of Phenylcarbene with Alcoholic Matrices
Authors: Tomioka Hideo , Ozaki Yasuji , Izawa Yasuji 
Published: July 2006

Abstract
Product analysis studies on the reaction of phenylcarbene in deuterated alcoholic matrices at 77 K revealed that isotope effect on O–H (D) insertion is very small while substantial isotope effect was observed for C–H (D) insertion.
A Convenient Synthesis of 2-Phenylbenzo[b]thiopyrylium Perchlorates
Authors: Nakazumi Hiroyuki , Ueyama Tamio , Endo Takashi , Kitao Teijiro 
Published: July 2006

Abstract
2-Phenylbenzo[b]thiopyrylium perchlorates were conveniently prepared in good yields by reduction of 2-phenyl-4H-benzo[b]thiopyran-4-ones (thioflavones) with aluminium hydride, followed by treatment with acid in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone.
Bromination of 4H-Cyclopenta[def]phenanthrenamines
Authors: Yoshida Masaaki , Minabe Masahiro , Ookawa Wataru , Suzuki Kazuo 
Published: July 2006

Abstract
Bromination of 4H-cyclopenta[def] phenanthren-1-amine, -2-amine, -3-amine, or -8-amine with bromine in chloroform took place at the 2-, 1-, 8-, or 9-position, respectively. The second bromine was introduced at the 8-, 3-, 2-, or 3-position. Similar regioselectivity was observed in the system of bromine in acetic acid–48% hydrobromic acid and of hydrobromic acid in dimethyl sulfoxide. The corresponding acetylamino compound was brominated at the same position as that of the parent amine.
Sesquiterpenoids in Cultured Cells of Liverwort, Calypogeia granulata INoue
Authors: Takeda Reiji , Katoh Kenji 
Published: July 2006

Abstract
Three new sesquiterpenoids, trinoranastreptene, 2-acetoxy-3-hydroxybicyclogermacrene and 3-acetoxy-2-hydroxybicyclogermacrene, were isolated from cultured cells of Calypogeia granulata INoue. Their structures have been established by spectroscopic analysis.
Synthesis of 2,2-Dimethyl-2H-pyran-fused Flavonols Using the Modified Algar-Flynn-Oyamada Reaction
Authors: Jain A C , Gupta S M , Sharma Anita 
Published: July 2006

Abstract
6-Acetyl-2,2-dimethylchromenes when separately condensed with p-anisaldehyde in the presence of ethanolic NaOH and subsequently oxidized with alkaline hydrogen peroxide without isolating the intermediate chalcones afforded the corresponding 2,2-dimethyl-2H-pyran-fused flavonols respectvely in good yield. Thus, flavonols having free 3-hydroxyl and fused with 2,2-dimethyl-2H-pyran can be synthesized easily.
On the Sorption Behaviour of Some Cations on Cobalt Hexacyanoferrate(III) Exchanger. Binary Separations of Rb+ and Cs+ on Columns
Authors: Jain Ajay K , Singh Rajpal , Bala Chand 
Published: July 2006

Abstract
Sorption behaviour of Ag, Cs, Rb, Co(II), Zn(II), and Fe(III) ions at low concentration (0.2 mmol) is studied in different concentrations of nitric acid and ammonium nitrate on cobalt hexacyanoferrate(III) exchanger. logKdvs. log concentration plots show that the sorption of these ions is not followed through ion exchange mechanism, only. In case of Rb+ and Cs+, a very low Kd is observed at high concentration of nitric acid (&gt;5 mol dm−3) thereby showing the possibility of their elution on columns. For various other ions, such as Ba, Sr, Mn, Hg(II), Mg, Cd, Ca, Pb, Ni, La, and Th, the Kd values are almost zero. Thus the binary separation of Rb+ and Cs+ from a number of ions on the columns of this exchanger has been carried out.
X-Ray Diffraction Study of Mixing States in the Carbon Tetrachloride Solutions of Methanol and Pentane
Authors: Tanaka Masami , Nishikawa Keiko , Tohji Kazuyuki , Fujiyama Tsunetake 
Published: July 2006

Abstract
A simple method has been proposed for estimating the state of mixing in a binary solution directly from the radial distribution function. The method has been applied to the estimation of the size of the cluster or aggregate in a binary solution of methanol and carbon tetrachloride. Pure liquid carbon tetrachloride and a binary solution of pentane and carbon tetrachloride have also been studied as reference systems. The number of methanol molecules which form a cluster in the solution at the volume ratio of 8.5(CCl4):1.5(CH3OH) has been estimated to be about 18, which is in good agreement with an estimate by light scattering.
The Conversion of CH3OH into Olefins over Al2O3–Cr2O3 Treated with CF3Cl
Authors: Kurosaki Akito , Okazaki Susumu 
Published: July 2006

Abstract
A mixed oxide of Al and Cr having an atomic ratio(Al/Cr) of around 9 showed catalytic activity for the conversion of CH3OH into olefins and aromatic compounds after treatment with CF3Cl at 450 °C. The mixed oxide treated with CF3Cl adsorbed a considerable amount of NH3, even at temperatures as high as 500 °C. Analyses of the compositions on the surface layer by using XPS showed that the F component was predominantly bound to Al, not to Cr. Strong acid sites related to the less crystallized AlF3 seemed to be able to promote the conversion of CH3OH.
Effect of Adsorption of Potassium Iodide on Catalytic Activity of Plate-type Raney Nickel
Authors: Yoshino Tomio , Abe Tuneyo 
Published: July 2006

Abstract
An experimental investigation was made of the adsorptive activity of Raney nickel catalyst toward potassium iodide over a wide KI concentration range and of the change with KI adsorption of hydrogenating activity toward unsaturated alcohol and ketone. Adsorbed amounts of K+ and I− ions were determined by potentiometry and radioactivity measurement. The adsorptive activity vs. I− concentration relation yields a definitive break at equilibrium concentration 5.5×105 mol dm−3 (surface coverage 26%), the adsorption features in the lower and higher ranges relative to the break point being approximately represented by Freundlich’s and BET equations, respectively. Adsorption sites effective for I− ion in the Freundlich region disappear almost completely when the catalyst is preheated at 600 °C. The surface coverage causing the hydrogenation activity to decrease by 50% is 3% for allyl alcohol and 0.3% for 2-butanone. With allyl alcohol, however, even such a catalyst as has preadsorbed ca. 5-monolayer amount of I− ions possesses a 33% residual activity, though catalyst coverages over 26% result in only a little decrease in activity. These results suggest that the adsorption sites in the Freundlich region may function as strong catalytically active centers for the hydrogenation, which are unstable to heating.
Suppression of Electroreductive Dimerization of Benzaldehyde by Addition of α-Cyclodextrin
Authors: Matsue Tomokazu , Tasaki Chikako , Fujihira Masamichi , Osa Tetsuo 
Published: July 2006

Abstract
The effect of α-cyclodextrin (α-CD) on the electroreduction of benzaldehyde was investigated. The reduction in aqueous system produces benzyl alcohol and 1,2-diphenyl-1,2-ethanediol (hydrobenzoin, dimerization product). The addition of α-CD caused the decrease in the yield of hydrobenzoin. This suppression effect was observed both in the controlled potential and controlled current electrolyses. This is accounted for by the retardation of the dimerization rate between the neutral radicals, since inclusion of substrate provides severe steric hindrance around the reaction site. The addition had only a small influence on the stereochemistry of hydrobenzoin formed by the dimerization.
The Molecular Structure of Bromo(ethyl)[(−)-sparteine]magnesium(II), a Catalyst for the Asymmetric-selective Polymerization of Racemic Methacrylates
Authors: Kageyama Hiroyuki , Miki Kunio , Tanaka Nobuo , Kasai Nobutami , Okamoto Yoshio , Yuki Heimei 
Published: July 2006

Abstract
The molecular structure of EtMgBr-(−)-sparteine, which initiates asymmetric (enantiomer) selective polymerization of racemic methacrylates, has been determined by means of X-ray diffraction. The crystal is orthorhombic, space group P212121, a=11.278(2), b=14.112(3), c=11.746(2) Å, Z=4. The structure was established by the heavy atom method and refined by the block-diagonal least-squares procedure: R=0.100 for 1272 non-zero reflections. The Mg atom is tetrahedrally coordinated by the Et group, Br and two N atoms of the (−)-sparteine.
The Low Lying Electronic States of Dichloromaleic Anhydride
Authors: Ishibashi Yoshimi , Shimada Ryoichi , Shimada Hiroko 
Published: July 2006

Abstract
The polarized Raman and infrared spectra of dichloromaleic anhydride were studied and the assignments of the normal vibrations were reinvestigated based on the polarization behaviors of the spectral bands and on the normal coordinate calculation. Using the assignments the vibrational structure of the phosphorescence spectrum was analyzed and the phosphorescence lifetime was also measured. These results indicate that the lowest triplet state of this molecule is a 3(π, π*) state perturbed by closely located 3(n, π*) states. The near ultraviolet absorption and phosphorescence excitation spectra were measured and four absorption bands due to 3(n, π*)←1A1, 1A2(n, π*)←1A1, 1B1(n, π*)←1A1, and 1A1(π, π*)←1A1 transitions were found. The polarization experiment made on the 1A2(n, π*)←1A1 absorption suggests that this transition borrows the intensity from the 1A1(π, π*)←1A1 transition.
Circular Dichroism Spectra and Racemization of Two Geometrical Isomers of the (2-Aminoethanesulfenato-S,N)[tris(2-aminoethyl)amine]cobalt(III) Ion
Authors: Kojima Masaaki , Fujita Junnosuke 
Published: July 2006

Abstract
Optically active trans(t-N,S)(t) and cis(t-N,S)(p) isomers of [Co{S(O)CH2CH2NH2}(tren)]2+ (tren=tris(2-aminoethyl)amine; t-N= tertiary amine nitrogen) were prepared, and their circular dichroism spectra were compared with those of Δ(S or R)- and Λ(S or R)-[Co{S(O)CH2CH2NH2}(en)2]2+ and two geometrical isomers of [Co(R-pn)(tren)]3+ (R-pn=(R)-1,2-propanediamine) and [Co(S-dmbn)(tren)]3+ (S-dmbn=(S)-3,3-dimethyl-1,2-butanediamine). Racemization or epimerization of these sulfenato complexes was studied in aqueous solutions with ionic strength of 1.0 (NaClO4) in the pH and temperature ranges of 3.65–8.8 and 24.0–40.0 °C, respectively. The rates of p- and t-isomers of the tren complex are proportional to concentrations of the complex, but independent of pH, the latter isomer accompanying some decomposition during the course of racemization. The first-order rate constants of the p- and t-isomers are 9.92×10−5 and ca. 1.2×10−6 s−1 at 30.0 °C, respectively. No epimerization takes place in the en complexes under the same experimental conditions. The difference in rate of racemization or epimerization of these sulfenato complexes seems to be related closely to the crowding around the S=O group of the complex.
Mixed-ligand Palladium(II) Complexes Containing O,O′-Chelated β-Diketonate and η3-Carbon-bonded Ethyl 3-Oxobutanoate Anions. Preparation and Reactions with Some Lewis Bases
Authors: Yamada Kurumi , Baba Shigeru , Nakamura Yukio , Kawaguchi Shinichi 
Published: July 2006

Abstract
Novel palladium(II) complexes [Pd(β-dik)(η3-etac)] (5), in which anions of a β-diketone and ethyl 3-oxobutanoate coordinate to the central metal atom by the O,O′-chelation and the η3 carbon bonding, respectively, were prepared by the reactions of a dinuclear complex [PdCl(η3-etac)]2 with thallium (I) β-diketonates in benzene or acetone at room temperature. Reactions of 5 with Lewis bases (L) such as triphenylphosphine, diethylamine, propylamine and benzylamine were investigated. In almost all reactions, only the η3-carbon-bonded ester ligand in 5 was converted into a terminal-carbon-bonded one to afford complexes [Pd(β-dik)(etac-C4)L]. The bonding modes for the ligands in these products as well as in 5 were determined by means of IR and 1H and 13C NMR spectroscopy.
Solvent Effects on the Extraction of Gallium(III) with Decanoic Acid
Authors: Yamada Hiromichi , Imai Shozo , Takeuchi Eiichi 
Published: July 2006

Abstract
Extraction of gallium(III) with decanoic acid (HA) in several solvents was carried out at 25 °C and at an aqueous ionic strength of 0.1 mol/dm3(NaClO4). Organic solvents used are toluene, chlorobenzene, 1,2-dichloroethane, and 1-octanol. Extracted species differs from solvent to solvent: Ga6A18(H2O)w for toluene, Ga3A9 for chlorobenzene, GaA3 and Ga3A9 for 1,2-dichloroethane and GaA2(OH), Ga2A4(OH)2 and Ga2A6 for 1-octanol. The less polar the solvent, the more extensive is the polymerization of the extracted species.
Reactions of Chloro[4-[2-(methylthio)anilino]-3-penten-2-onato-O,N,S]palladium(II) with Carbanions and Pyridine Derivatives
Authors: Hiraki Katsuma , Onishi Masayoshi , Hayashida Minoru , Kurita Kyogo 
Published: July 2006

Abstract
A Schiff base, 4-[2-(methylthio)anilino]-3-penten-2-one (Hmtap), prepared from acetylacetone and 2-(methylthio)aniline, reacted with Na2[PdCl4] in the presence of sodium ethoxide to give [PdCl(mtap-O,N,S)] (1). Complex 1 was treated with carbanions formed from dimethyl malonate, methyl cyanoacetate, and malononitrile in the presence of sodium methoxide to afford the corresponding (disubstituted methyl)palladium(II) complexes, [Pd(CHYY′)(mtap-O,N,S)] (Y,Y′=COOMe and/or CN). On the other hand, 1 reacted with Tl(acac) to yield an O,O′-chelating complex, [Pd(mtap-N,O)(acac)], in which the mtap moiety served as a bidentate ligand. Moreover, 1 reacted with 2,2′-bipyridine (bpy) and 4-(dimethylamino)pyridine (dmapy) in the presence of NaClO4·H2O to give [Pd(mtap-N,O)(bpy)]ClO4 and [Pd(mtap-O,N,S)(dmapy)]ClO4, respectively. These complexes are characterized by means of elemental analysis and IR and NMR spectroscopy.
A Convenient Method for the Synthesis of Adenylyl-(2′–5′)-adenylyl(2′–5′)-adenosine Using 3′-O-Benzoyladenosine Derivatives
Authors: Takaku Hiroshi , Ueda Souichi 
Published: July 2006

Abstract
N 6,3′-O-Dibenzoyladenosine was prepared by treating 2′,3′-O-(dibutylstannylene)-N6-benzoyladenosine with benzoyl chloride in methanol. The trimeric adenylyl-(2′–5′)-adenylyl-(2′–5′)-adenosine was synthesized in a good yield using N6,3′-O-dibenzoyladenosine as the starting material via the phosphotriester approach.
Oxygen Promoted Addition of 1,3-Dioxolane to Electron-deficient Alkenes
Authors: Watanabe Yoshihisa , Tsuji Yasushi , Takeuchi Ryo 
Published: July 2006

Abstract
1,3-Dioxolane reacted with electron-deficient alkenes, such as diethyl maleate, maleic anhydride, diethyl fumarate and fumaronitrile, under an oxygen atmosphere or in air to give 1:1 adducts in good to excellent yields. The presence of oxygen promoted the reaction. The reaction appears to be characteristic of 1,3-dioxolane. Methylal and ethylal did not react with diethyl maleate under the same conditions.
Pseudo-sugars. VIII. Synthesis of Dl-1-Epivalidamine and Related Compounds
Authors: Ogawa Seiichiro , Oya Masayuki , Toyokuni Tatsushi , Chida Noritaka , Suami Tetsuo 
Published: July 2006

Abstract
Dl-1-Epivalidamine has been synthesized starting from the dianhydro compound derived from Dl-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol. Dl-7-Amino-7- deoxy-1-epivalidamine, which is considered to be a homolog of 2-deoxystreptamine, has also been prepared.
Regio-controlled Prenylation and Geranylation of 3-Furylmethylmagnesium Bromide. Selective Syntheses of 3-Substituted Furanoid and 2-Substituted 3-Methylfuranoid Terpenes
Authors: Araki Shuki , Butsugan Yasuo 
Published: July 2006

Abstract
Coupling reactions of 3-furylmethylmagnesium bromide with prenyl and geranyl diethyl phosphates gave 2-substituted 3-methylfurans, rosefuran and sesquirosefuran, as the main products. When the reactions were carried out in the presence of a catalytic amount of copper(I) iodide, normal coupling occurred and 3-substituted furans, perillene and dendrolasin, were formed in good yields. The related naturally occurring 3-substituted thiophene, 3-(4-methyl-3-pentenyl)thiophene, was also synthesized from 3-thienylmethylmagnesium bromide and prenyl diethy phosphate.