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  4. 2004
Showing papers on "Polycyclic compound published in 2004"
Journal Article•10.1021/JA051171C•
Total synthesis of brevetoxin B

[...]

Isao Kadota1, Hiroyoshi Takamura1, Hiroki Nishii1, Yoshinori Yamamoto1•
Tohoku University1
19 Oct 2004-Journal of the American Chemical Society
TL;DR: The convergent total synthesis of brevetoxin B has been achieved and the intramolecular allylation of the O,S-acetal 20, prepared from the alpha-chlorosulfide 17 and the alcohol 5, was carried out using AgOTf as a Lewis acid to give the diene 21.
Abstract: Brevetoxin-B (BTX-B), produced by the red tide organism, Gymnodium breve Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature is a trans-fused polycyclic ether ring system with 23 stereocenters. Its unique, complex structure and potent biological activity have attracted the attention of synthetic organic chemists. Total synthesis of BTX-B has been accomplished via the coupling of the ABCDEFG and IJK-ring segments, each ether ring of which was stereoselectively and efficiently constructed on the basis of SmI2-induced intramolecular cyclization, 6-endo-cyclization of hydroxy epoxide, ring-closing olefin metathesis, and SmI2-induced intramolecular Reformatsky-type reaction. Several kinds of double reactions at the left and right sides were efficiently used through the synthesis.

128 citations

Journal Article•10.1021/JO048788H•
Synthesis of fused polycycles by 1,4-palladium migration chemistry.

[...]

Qinhua Huang1, Marino A. Campo1, Tuanli Yao1, Qingping Tian1, Richard C. Larock1 •
Iowa State University1
26 Oct 2004-Journal of Organic Chemistry
TL;DR: Novel palladium migration/arylation methodology for the synthesis of complex fused polycycles has been developed, in which one or more sequential Pd-catalyzed intramolecular migration processes involving C-H activation are employed.
Abstract: Novel palladium migration/arylation methodology for the synthesis of complex fused polycycles has been developed, in which one or more sequential Pd-catalyzed intramolecular migration processes involving C-H activation are employed. The chemistry works best with electron-rich aromatics, which is in agreement with the idea that these palladium-catalyzed C-H activation reactions parallel electrophilic aromatic substitution.

85 citations

Journal Article•10.1021/JA045532K•
Ruthenium- and platinum-catalyzed sequential reactions: selective synthesis of fused polycyclic compounds from propargylic alcohols and alkenes.

[...]

Yoshiaki Nishibayashi1, Masato Yoshikawa1, Youichi Inada1, Masanobu Hidai1, Sakae Uemura1 •
Tokyo University of Science1
18 Nov 2004-Journal of the American Chemical Society
TL;DR: A simple method for the preparation of fused polycyclic compounds by an intramolecular cyclization of propargylic alcohols bearing an alkene moiety at a suitable position has been developed, where the presence of both Ru and Pt catalysts promotes a sequence of catalytic cycles in the same medium.
Abstract: A simple method for the preparation of fused polycyclic compounds by an intramolecular cyclization of propargylic alcohols bearing an alkene moiety at a suitable position has been developed, where the presence of both Ru and Pt catalysts promotes a sequence of catalytic cycles in the same medium. This sequential system can be applied to an intermolecular reaction between a propargylic alcohol and an alkene to obtain the corresponding bicyclo[3,1,0]hex-2-ene derivative. These sequential reactions provide a conceptually new type of cycloaddition system between propargylic alcohols and alkenes.

75 citations

Journal Article•10.1021/JA047826B•
A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.

[...]

Kosuke Namba1, Hyuk-Sang Jun1, Yoshito Kishi1•
Harvard University1
03 Jun 2004-Journal of the American Chemical Society
TL;DR: A simple device consisting of two ion-exchange columns, two alumina-based filters, and a pump was assembled to form the C8-C14 polycyclic ring system present in the halichondrin B class of marine natural products.
Abstract: A simple device consisting of two ion-exchange columns, two alumina-based filters, and a pump (Figure 1) was assembled to form the C8-C14 polycyclic ring system present in the halichondrin B class of marine natural products. The effectiveness of this device was tested for three substrates. In each case, the desired polycyclic ketal 3, 5, or 7 was obtained almost quantitatively in a single operation.

40 citations

Journal Article•10.1021/JO035606V•
Synthetic approaches to indolo[6,7-a]pyrrolo[3,4-c]carbazoles: potent cyclin D1/CDK4 inhibitors.

[...]

Margaret M. Faul, Thomas A. Engler, Kevin A. Sullivan, John L. Grutsch, Marcella T. Clayton, Michael John Martinelli, Joseph Matthew Pawlak, Michael E. LeTourneau, D. Scott Coffey, Steven Wayne Pedersen, Stanley P. Kolis, Kelly Wayne Furness, Sushant Malhotra, Rima S. Al-awar, James Edward Ray 
31 Mar 2004-Journal of Organic Chemistry
TL;DR: The chemistry developed enabled introduction of functionality (-OR, NR(2)) at C(12) and N(13) facilitating structure-activity relationship (SAR) evaluation of this indolocarbazole platform.
Abstract: Synthesis of indolo[6,7-a]pyrrolo[3,4-c]carbazoles 1, a new class of cyclin D1/CDK4 inhibitors, by oxidation of the corresponding aryl indolylmaleimides 2, will be described. Two approaches to the ...

38 citations

Journal Article•10.1021/JO035748P•
Synthesis of Highly Branched Sulfur−Nitrogen Heterocycles by Cascade Cycloadditions of [1,2]Dithiolo[1,4]thiazines and [1,2]Dithiolopyrroles

[...]

Susana Barriga1, Pedro Fuertes1, Carlos F. Marcos1, Tomás Torroba1•
University of Extremadura1
23 Apr 2004-Journal of Organic Chemistry
TL;DR: Cyclic voltammetry of selected examples showed irreversible processes that were not influenced by peripheral groups bonded to the heterocyclic system, and Reaction conditions were crucial for achievement of selectivity in thermal reactions.
Abstract: We report the synthesis of some new polysulfur-nitrogen heterocycles by cascade cycloadditions to readily available polycyclic 1,2-dithiole-3-thiones. Thus, treatment of bis[1,2]dithiolopyrrole dithione 1 with dimethyl acetylenedicarboxylate (DMAD) or dibenzoylacetylene (DBA) gave the 1:4 adducts 2a,b and 3a. On the other hand, cycloaddition of bis[1,2]dithiolo[1,4]thiazine dithiones 4a-d with the same dipolarophiles gave the 1:2, 1:3, or 1:4 adducts 5a-c, 6a, 7a, 8a, 9a, and 10a,c,d selectively in fair to high yields. Reaction conditions were crucial for achievement of selectivity in thermal reactions. Catalysis by scandium triflate was used in the reaction of 4a and 2 equiv of DMAD. Treatment of the [1,2]dithiolo[1,4]thiazine dithione 11 with DBA gave the 1:2, 1:3 (two isomers), and 1:4 adducts 12-14 and 15a-d selectively. Cyclic voltammetry of selected examples showed irreversible processes that were not influenced by peripheral groups bonded to the heterocyclic system.

23 citations

Patent•
Fluorinated photoresists prepared, deposited, developed and removed in carbon dioxide

[...]

Joseph M. DeSimone1, Luke A. Zannoni1, Evan Hicks1, Colin D. Wood1•
University of North Carolina at Chapel Hill1
20 Oct 2004
TL;DR: In this paper, a terpolymer is defined as a linear or branched compound that has at least one fluorine atom covalently coupled to a polycyclic compound.
Abstract: The present invention provides a compound that is a terpolymer of: (a) at least one ethylenically unsaturated linear or branched compound that has at least one fluorine atom covalently coupled thereto; (b) at least one ethylenically unsaturated precursor of a cyclic or polycyclic compound that has at least one fluorine atom covalently coupled thereto forming a cyclic or polycyclic decrystallizing monomer in said terpolymer; and (c) at least one ethylenically unsaturated functional compound which as a monomer in said terpolymer changes solubility upon exposure to an acid or base. Methods of making and using such compounds in photolithography are also described.

13 citations

Patent•
Light-emitting device, condensed polycyclic compound used therein and method for producing same

[...]

Masaaki Ikeda, Takaaki Kurata, Teppei Tsuchida, Chihaya Adachi
16 Jan 2004
Abstract: A device which emits a light using an electric energy and in which device an organic thin film including a light emission layer is formed between an anode and a cathode is characterized by containing at least a compound which has a basic skeleton represented by the general formula (1) or (2) shown below. By using a condensed polycyclic compound of the present invention, a light-emitting device can have a high color purity, a high luminance, and a high efficiency.

13 citations

Journal Article•10.1016/J.SYNTHMET.2004.07.009•
Surface-induced vertical alignment of self-assembled supramolecular columns of large polycyclic aromatic hydrocarbons and porphyrins

[...]

Rainer Friedlein1, Xavier Crispin1, Wojciech Osikowicz1, Slawomir Braun1, M. P. de Jong1, Christopher D. Simpson2, Mark D. Watson2, F. von Kieseritzky3, Paolo Samorì4, Stina Jönsson1, Mats Fahlman1, Frank Jäckel4, Jürgen P. Rabe4, Jonas Hellberg3, Klaus Müllen2, William R. Salaneck1 •
Linköping University1, Max Planck Society2, Royal Institute of Technology3, Humboldt University of Berlin4
07 Dec 2004-Synthetic Metals
TL;DR: In this paper, a vertical growth of self-assembled supramolecular columns perpendicular to the basal plane of the substrate along with their lateral ordering on the surface has been achieved.

12 citations

Patent•
Curable polycyclic compound and its preparation process

[...]

Junji Takenaka, Tanaka Kenji, Hiromasa Yamamoto, 博将 山本, 健次 田中, 潤治 竹中 
17 Jun 2004
TL;DR: In this article, the curable polycyclic compound is shown by formula (1) [wherein A represents a bi-to hexa-valent group derived from the polycyclIC hydrocarbon compounds; R 1 represents an optionally perfluorinated 1-4C alkyl group or fluorine atom; n represents an integer of 0-2; m represents aninteger of 2-4; Y represents a formula (2, or (3) (wherein R 2, R 3, R 5 and R 6 are each independently representing hydrogen or a fluorine
Abstract: PROBLEM TO BE SOLVED: To provide an industrially useful novel curable compound having a polycyclic hydrocarbon structure in the molecule and excellent in such as light and heat resistances with abundant applicable techniques. SOLUTION: The curable polycyclic compound is shown by formula (1) [wherein A represents a bi- to hexa-valent group derived from the polycyclic hydrocarbon compounds; R 1 represents an optionally perfluorinated 1-4C alkyl group or fluorine atom; n represents an integer of 0-2; m represents an integer of 2-4; Y represents a formula (2) or (3) (wherein R 2 , R 3 , R 5 and R 6 are each independently represents hydrogen or a fluorine atom or a 1-4C alkyl group; R 4 represents a methyl or ethyl group; p and q each represent an integer of 0-4)]. COPYRIGHT: (C)2005,JPO&NCIPI

11 citations

Patent•
Condensed polycyclic compound and organic light-emitting element by using the same

[...]

Koichi Suzuki, Akito Saito, Naoki Yamada, Kawai Tatsuto, Maki Kasahara, Akihiro Senoo 
8 Apr 2004
TL;DR: In this article, a condensed polycyclic compound and an organic light-emitting element having light output with an extremely high efficiency and high luminance and also having an extreme durability by using the same.
Abstract: PROBLEM TO BE SOLVED: To provide a new condensed polycyclic compound and an organic light-emitting element having light output with an extremely high efficiency and high luminances and also having an extreme durability by using the same. SOLUTION: This condensed polycyclic compound is expressed by general formula [I] (wherein, R 1 is H, a substituted or non-substituted alkyl, a substituted or non-substituted aralkyl, a substituted or non-substituted aryl, a substituted or non-substituted heterocyclic group, a substituted amino, cyano or a halogen atom; and Ar 1 to Ar 5 are each a substituted or non-substituted condensed polycyclic aromatic group, or a substituted or non-substituted condensed polyheterocyclic group and allowed to be the same or different). The compound is used as an electron-transporting layer or a light-emitting layer of the organic light-emitting element. COPYRIGHT: (C)2004,JPO
Patent•
Transalkylation of aromatic fluids

[...]

Richard H. Schlosberg, Edmund J. Mozeleski, Francisco M. Benitez, Steven M Silverberg, Terry E. Helton 
1 Apr 2004
TL;DR: In this article, a process for making an ethylated polycyclic aromatic compound in a mixed aromatic fluid, the process comprising contacting the mixed aromatic mixture containing a polycyclically aromatic compound and a monocyclic compound having an anisotropic substituent in the presence of an acid catalyst under conditions sufficient to effect transalkylation to form the ethylation of the compound and the removal of the de-ethylated compound.
Abstract: A process for making an ethylated polycyclic aromatic compound in a mixed aromatic fluid, the process comprising contacting the mixed aromatic fluid containing a polycyclic aromatic compound and a monocyclic aromatic compound having an ethyl substituent in the presence of an acid catalyst under conditions sufficient to effect transalkylation to form the ethylated polycyclic compound and a de-ethylated monocyclic aromatic compound and removal of the de-ethylated monocyclic aromatic compound. A process for decreasing naphthalene concentration in a naphthalene-containing aromatic fluid by acid catalyzed transalkylation of an alkylbenzene and naphthalene to form benzene and an alkylnaphthalene.
Journal Article•10.1021/JO030349F•
Reactions of Sterically Congested 1,5-Hexadienes: Ab Initio and DFT Calculations on the Competition between Cope Rearrangements and Disrotatory Cyclobutene Ring-Opening Reactions of Bridged syn-Tricyclo[4.2.0.02,5]octa-3,7-dienes

[...]

Sabine Bethke1, David A. Hrovat1, Weston Thatcher Borden1, Rolf Gleiter1•
University of Washington1
16 Apr 2004-Journal of Organic Chemistry
TL;DR: Calculated thermolytic behavior of four syn-tricyclo[4.2.0.0(2,5)]octa-3,7-dienes, each spanned by four propano bridges, is found to be in very good agreement with the results of experiments on these hydrocarbons.
Abstract: The thermolytic behavior of four syn-tricyclo[4.2.0.02,5]octa-3,7-dienes, each spanned by four propano bridges (13, 14, 21, and 26), has been investigated by means of calculations at the UB3LYP/ 6-31G* and CASPT2/6-31G* levels. These calculations predict that 13 should undergo a degenerate Cope rearrangement (EA = 19.6 kcal/mol), whereas the other three C20H24 isomers should prefer a necessarily disrotatory cyclobutene ring-opening reaction. In the case of 14, the ring-opening reaction (EA = 27.2 kcal/mol) is concerted and leads directly to 15, a 4-fold bridged cyclooctatetraene. In the ring opening of 21, the 1,6-bridge in the 4-fold bridged bicyclo[4.2.0]octa-2,4,7-triene 31 prevents formation of the corresponding cyclooctatetraene. In the ring opening of 26, the 4-fold bridged bicyclo[4.2.0]octa-2,4,7-triene derivative 36 is predicted to form the corresponding bridged cyclooctatetraene 38, which should undergo bond shift. The results of these calculations are found to be in very good agreement with the...
Journal Article•10.1021/JO0493626•
Pyramidalized olefins: a DFT study of bicyclo[2.1.1]-, -[3.2.1]-, and -[3.2.2]alkenes and their fused derivatives. Two rare examples of pi-facially symmetric pyramidal olefins.

[...]

Richard V. Williams1, Davor Margetić•
University of Idaho1
15 Oct 2004-Journal of Organic Chemistry
TL;DR: Density functional theory (B3LYP/6-31G) was used to study a large series of bridged polycyclic alkenes based on the bicyclo, finding the preference for propano-directed bending in the bicycleo[3.2.1.1]octenes is about as strong as that for endo bending in norbornenes.
Abstract: Density functional theory (B3LYP/6-31G) was used to study a large series of bridged polycyclic alkenes based on the bicyclo[2.1.1], -[3.2.1], and -[3.2.2] nuclei. In those compounds with pi-facial dissymmetry, butterfly bending of the strained olefinic bonds was generally predicted. Surprisingly, large pyramidalizations are calculated for the highly strained but pi-facially symmetric tetracyclo[5.1.1.1.(3,5)0(2,6)]dec-2-ene (28, psi = 19.8 degrees ) and tetracyclo[5.2.2.1.(3,5)0(2,6)]dodec-2,8,10-triene (33, psi = 14.4 degrees ). The preference for propano-directed bending in the bicyclo[3.2.1]octenes is about as strong as that for endo bending in norbornenes.
Patent•
Novel fused polycyclic compound having heterocycle and medicinal use thereof

[...]

Ryusuke Hirama1, Seiji Niwa1, Hideyuki Tanaka1, Toshihiro Hatanaka1, Yoko Masuzawa1, Akiyo Yamazaki1, Takao Ikenoue1, Nobuo Kondo1, Wataru Miyanaga1, Masaru Takayanagi1 •
Ajinomoto1
1 Nov 2004
TL;DR: A fused polycyclic compound represented by the following formula, an analogue thereof, and a pharmaceutically acceptable salt of either; and a sugar transportation enhancer, hygroglycemic agent, and medicinal composition each containing any of these.
Abstract: A fused polycyclic compound represented by the following formula, an analogue thereof, and a pharmaceutically acceptable salt of either; and a sugar transportation enhancer, hygroglycemic agent, and medicinal composition each containing any of these. The fused polycyclic compound is highly effective in treatments for diabetes and is reduced in side effects. (I) (In the formula, R represents alkoxy, R' represents oxazolylpropoxy or thiazolylpropoxy, and R' represents hydrogen.)
Patent•
Pharmaceutical preparations containing arginine amides

[...]

Kazuhiko Ozaki, Manami Hiramiya, Katsuyoshi Yoshizawa, Takashi Yamada, Takeshi Hirokawa, Kouichi Sugawara, Katsunori Kurusu, Noboru Yamada, Kenichi Kajihara 
19 Mar 2004
TL;DR: A pharmaceutical preparation comprising a solution which contains as the active ingredient a substance selected from the group consisting of arginine amides represented by the general formula (I), salts thereof, and hydrates of both in a concentration of 1 to about 10mg/mL (with the proviso that the solution must contain at least water) and is packed in a container having a capacity of about 1 to 20 mL as discussed by the authors.
Abstract: A pharmaceutical preparation comprising a solution which contains as the active ingredient a substance selected from the group consisting of arginine amides represented by the general formula (I), salts thereof, and hydrates of both in a concentration of 1 to about 10mg/mL (with the proviso that the solution must contain at least water) and is packed in a container having a capacity of about 1 to about 20 mL: (I) [wherein R1 is (2R, 4R)-4-alkyl-2-carboxypiperidino; and R2 is phenyl or a residue of a fused polycyclic compound, and R2 may have one or more substituents selected from among lower alkyl, lower alkoxy, and amino groups susbstituted with lower alkyl groups, with the provisos that the residue of a fused polycyclic compound bears a benzene ring and the benzene ring is bonded to the sulfonyl sulfur in the general formula (I) and fused with other rings including heterocycles and that the total number of ring-constituting carbon atoms of the residue is 7 to 14]. The pharmaceutical preparations and pharmaceutical compositions of the invention have advantages of high convenience and safety in medical service, good storage stability, and easy and simple producibility.
Patent•
Fluorine-containing polycyclic compound, polymer compound using it as raw material and photoresist material using it

[...]

Miyazawa Satoru, Komoriya Haruhiko, Maeda Kazuhiko
2 Apr 2004
TL;DR: In this article, a series of new fluorine-containing tricyclonononene compounds are synthesized and polymers using these monomers are shown to have a good film-forming ability and high etching resistance.
Abstract: PROBLEM TO BE SOLVED: To provide a new fluorine-containing compound and a polymer compound using it. SOLUTION: A series of new fluorine-containing tricyclononene compounds as specific compounds having a tricyclic skeleton and a high fluorine content and containing a hydroxy group(s) and polymers using these monomers are synthesized. The fluorine-containing tricyclononene compounds being new polymerizable monomers and the polymer compounds using the monomers are highly transparent to a wide range of wavelengths from the vacuum-ultraviolet region to the optical communication region in spite of their high fluorine content because of the presence of polar groups in the same molecule, have a close adhesion to substrates and a good film-forming ability and a high etching resistance because of their alicyclic structure. COPYRIGHT: (C)2004,JPO
Patent•
Polycyclic compound and manufacturing method therefor

[...]

Keisuke Suzuki, Bode Jeffrey W
20 May 2004
TL;DR: In this paper, a polycyclic compound is represented by formula (I), where R 1 is a hydrogen atom, a halogen atom, hydroxyl group, an optionally substituted 1-10C alkoxyl group or an optionally substituting 1-20C hydrocarbon group.
Abstract: PROBLEM TO BE SOLVED: To obtain an intermediate for synthesizing a pharmaceutical compound, an agrochemical compound, a dye compound, a compound for a photographic material, and the like, each having an anthraquinone skeleton, and a manufacturing method therefor. SOLUTION: The subject polycyclic compound is represented by formula (I) (wherein R 1 is hydrogen atom, a halogen atom, hydroxyl group, an optionally substituted 1-10C alkoxyl group or an optionally substituted 1-20C hydrocarbon group; R 2 is a halogen atom, hydroxy group, cyano group, nitro group, an optionally substituted amino group, an optionally substituted 1-10C alkoxyl group, an optionally substituted 1-10C acyl group, an optionally substituted 1-20C hydrocarbon group, an optionally substituted 5 to 7-membered heterocyclic group, or the like; R 3 is a halogen atom, hydroxy group, an optionally substituted 1-10C alkoxycarbonyl group, an optionally substituted 6-20C hydrocarbon group, or the like; (m) is an integer of 0-3; and (n) is an integer of 0-6). The manufacturing method for the polycyclic compound is also provided. COPYRIGHT: (C)2004,JPO
Patent•
Method for producing (meth)acrylic esters

[...]

Sumiya Naoko, Kusaka Haruhiko, Okago Yuji
22 Apr 2004
TL;DR: In this article, the authors proposed a method for producing high-purity (meth)acrylic esters useful as fine chemicals such as medicines, agrochemicals or photoresist raw materials in good yields in a simpler manner.
Abstract: PROBLEM TO BE SOLVED: To produce high-purity (meth)acrylic esters useful as fine chemicals such as medicines, agrochemicals or photoresist raw materials in good yields in a simpler manner as compared with that of the conventional method by reacting a polycyclic compound having an acrylate or a methacrylate group and a carboxy group with an olefin in the presence of an acidic catalyst. SOLUTION: The method for producing the (meth)acrylic esters comprises reacting the polycyclic compound having the (meth)acrylate group and carboxy group with the olefin in the presence of the acidic catalyst and esterifying the carboxy group in the polycyclic compound. COPYRIGHT: (C)2004,JPO
Patent•
Oxygen atom-containing polycyclic compound, polymerizable composition and cured product thereof

[...]

Tomoko Adachi, Takahiro Iwahama, 隆裕 岩浜, 知子 足立
31 Aug 2004
TL;DR: In this paper, the problem of obtaining a new oxygen-containing polycyclic compound, a polymerizable composition comprising the same and a cured product thereof, was solved by finding a new polymerizable solution.
Abstract: PROBLEM TO BE SOLVED: To obtain a new oxygen-containing polycyclic compound, a polymerizable composition comprising the same and a cured product thereof. SOLUTION: The oxygen-containing polycyclic compound is represented by formula (I) (ring Z is a polycyclic nonaromatic ring containing one oxygen atom on a part of a ring; X and RO-(W) n -group is a substituent group bonded to a carbon atom constituting ring Z; X is a halogen atom, an alkyl group, a haloalkyl group, an aryl group, a sulfo group, an oxo group, a nitro group, a cyano group or a hydroxy group which may be protected with a protective group or the like; W is a bifunctional organic group; R is a hydrogen atom or a group represented by formula (2); p is an integer of ≥0; n is 0 or 1; m is an integer of 1-5; s and t are each an integer of 0-7 or the like; R 1 , R 2 and R 3 are each the same or different and a hydrogen atom or a 1-4C alkyl group). COPYRIGHT: (C)2006,JPO&NCIPI
Journal Article•10.1021/JE049879E•
Ionic liquids/water distribution ratios of some polycyclic aromatic hydrocarbons

[...]

Jingfu Liu1, Yu-guang Chi1, Jin-feng Peng1, Guibin Jiang1, Jan Åke Jönsson1 •
Chinese Academy of Sciences1
19 Aug 2004-Journal of Chemical & Engineering Data
TL;DR: In this paper, the distribution ratios of polycyclic aromatic hydrocarbons (PAHs) between room-temperature ionic liquids, 1-alkyl-3-methylimiazolium hexafluorophosphates ([CnMIM] [PF6], n = 4 and 8), and water were determined.
Abstract: By using the shake-flask procedure, the distribution ratios (D) at infinite dilution and 298.1 K of 15 polycyclic aromatic hydrocarbons (PAHs) between room-temperature ionic liquids, 1-alkyl-3-methylimiazolium hexafluorophosphates ([CnMIM] [PF6], n = 4 and 8), and water were determined. The log D values are in the range of 3.34-4.36, which increased very slowly with the molar mass of PAHs.
Journal Article•10.1021/JO049253R•
General approach to polycyclic meroterpenoids based on stille couplings and titanocene catalysis

[...]

José Justicia1, J. Enrique Oltra1, Juan M. Cuerva1•
University of Granada1
23 Jul 2004-Journal of Organic Chemistry
TL;DR: A novel convergent procedure that has proved useful in the synthesis of a wide range of meroterpenoid-related structures containing a mono-, sesqui-, or diterpenoid moiety linked to a nonfused aromatic subunit with various substitution patterns is described.
Abstract: We describe a novel convergent procedure that has proved useful in the synthesis of a wide range of meroterpenoid-related structures containing a mono-, sesqui-, or diterpenoid moiety linked to a nonfused aromatic subunit with various substitution patterns. The key steps were the Stille-type coupling of aryl stannanes and allylic carbonates, followed by the titanocene-catalyzed domino cyclization of aryl epoxypolyprenes. The coupling reaction was perfectly compatible with preformed epoxides, while the sequential cyclization, which presumably proceeded via alkyl radicals inert to benzene derivatives, selectively provided exocyclic alkenes.

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