Novel preparation of 1- and 3-substituted bicyclo[3.2.2]nona-3,6,8-trien-2-ones from tropones and 2,3-bis(methoxycarbonyl)-7-oxabicyclo-[2.2.1]heptadiene by high-pressure cycloaddition-thermal cycloreversion procedure.
スポンサーリンク
概要
- 論文の詳細を見る
The Diels–Alder adduct of tropone with 2,3-bis(methoxycarbonyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene formed homobarrelenone on heating at 130 °C. Similarly prepared were 1-hydroxy-, 3-methoxy-, 1-chloro-, and 3-chlorohomobarrelenones. High-pressure cycloaddition improved the yields of the Diels–Alder adducts. In reactions of 2-methoxy- and 2-chlorotropones with the 7-oxanorbornadiene derivative, the endo-isomers were predominantly produced together with the exo-isomers.
- 公益社団法人 日本化学会の論文
著者
-
Takeshita Hitoshi
Institute Of Advanced Material Study 86 Kyushu University
-
Mori Akira
Institute For Materials Chemistry And Engineering Kyushu University
-
Mori Akira
Institute of Advanced Material Study, 86, Kyushu University
-
Tian Guan
Institute of Advanced Material Study, 86, Kyushu University
-
Sugiyama Shigeru
Institute of Advanced Material Study, 86, Kyushu University
関連論文
- Synthesis, Crystal Structure, and Mesomorphic Properties of Liquid Crystals with a Bis(tropon-2-yl)-4,4’-azobisbenzoate Core
- Synthesis and Properties of Columnar Liquid Crystals and Organogelator with a Bitropone Core
- Synthesis and Properties of Cholesteryl Benzoate Derivatives : Liquid Crystals and Organogelators
- Synthesis and Mesomorphic Properties of Tropon-4-yl 4-n-Alkoxybenzoates : Roles of a Tropone Ring as a Polar Terminal Group
- Synthesis, Complexation Behaviors, and Crystal Structures of Azamacrocycles Having Tropon-2-yl Groups
- Synthesis, Structure, and Mesomorphic Properties of Liquid Crystals with a Bitropone Core
- Synthesis, Crystal Structures and Mesomorphic Properties of Liquid Crystals with a N,N'-Bis(tropon-2-yl)piperazine Skeleton
- Lead(IV) Oxide-Mediated Oxidation of Azulen-2-ols to Form 1,1-Coupled Dimers and Hexacyclic Cage-Dimers
- Novel Non-benzenoid Electron Acceptors:Syntheses and Electron Acceptability of Tetracyanoazulenequinodimethanes and Dicyanoazulenequinonemethides
- A New Mercurophilic Troponoid Tetrathiacyclophane;2, 6, 8, 12-Tetrathia-1(2, 7), 7(2, 7)-ditropona-4(1, 3), 10(1, 3)-dibenzenacyclododecaphane
- Synthesis and Properties of Bis(5-alkoxytropolonato) Metallomesogens
- Evaluation of Lewis Acidity of "Naked"Lithium Ion through Diels-Alder Reaction Catalyzed by Lithium TFPB in Nonpolar Organic Solvents
- Synthesis and Mesomorphic Properties of Liquid Crystals with a 5,5'-Bitropolone Skelton
- Synthesis of 9-Deoxycotylenol Derivatives and Their Seed Germination-Stimulating Activity
- Inner Rotation of the Exocyclic C=C Bonds of Methyl 2-Cyano-(2-methyl-cyclohepta[b]thiophen-8-ylidene)acetate and Methyl 2-Cyano-(1,2-dimethylcyclohepta[b]pyrrol-8-ylidene)acetate
- A New Convenient Synthesis of 1,2′-Biazulenes by Photolysis of 2-Diazo-1,3-dicyanoazulen-6(2H)-one with Azulene Derivatives
- Crucial Role of the Tropone C=O Group in Preferential Exhibition of Smectic C Phase through Intermolecular Hydrogen Bonding
- Mesomorphic Properties of 4-Benzoylaminobenzonitrile Derivatives Having an Electron-withdrawing Group with Hydrogen Bonding Ability
- Liquid Crystals with a 5-Cyanotropone Skeleton: 2-(4-Alkoxybenzoyloxy)-5-cyanotropones and 2-(4-Alkoxybenzoylamino)-5-cyanotropones
- Preparation of Sigmatropic 2-Acyloxy-5-perfluoroalkoxytropones : New Monocyclic Troponoid Liquid Crystals with an Enantiotropic Smectic A Phase
- Synthesis of 9-Deoxy-15-hydroxycotylenol and Its Germination-Stimulating Activity on Lettuce Seeds
- Photodimerizations of 1,5- and 1,7-Azulenequinones : Solvent, Substituent, and Concentration Effects on the Product Distribution
- Mesomorphic Properties of Bis(5-alkoxy-2-aminotroponato)coppers and Their N,N-Dimethyl Derivatives
- Appearance of the Induced Smectic A Phase in the Binary System between Two Troponoid Twins with the Opposite Dipole Moment
- New Twin-Type Troponoid Liquid Crystals with a Smectic C Phase
- Total Synthesis of Sollasin a and Sollasin d via Photocycloaddition of Methyl 2, 4-Dioxopentanoate to Methyl E-2-Methyl-2-butenoate
- Crystal Structures of 2-Aminotropone, N,N’-Di(tropon-2-yl)piperazine, and 5-(4-Ethoxyphenylazo)tropolone
- Synthesis and Mesogenic Properties of New Non-Sigmatropic, Monocyclic Troponoids, 5-Acyloxy-2-alkoxytropones
- Highly Thermally-Stable Diels-Alder Adducts of [60]Fullerene with 2-Cycloalkenones and Their Acetals
- Preparation of Tetraphenylazulenequinodimethanes from the Reactions of Azulenequinones with Diphenylketene and the ^1H NMR and UV-vis Spectral Studies in Acidic Media
- New Troponoid Liquid Crystalline Compounds, 5-Alkoxy-2-(4-alkoxybenzoylamino)tropones
- Synthesis and Mercurophilic Properties of 2,2'-Oxybis(ethylenethio)ditropone and α-[2-(2-Troponylthio)ethyl]-ω-(2-troponylthio)oligo(oxyethylene)
- Photodimerizations of 3-Methoxy-1, 5-azulenequinone via Consecutive Pericyclic Reactions
- Mesogenic Properties of Tricyclic 2, 5-Di(4-alkoxybenzoyloxy)tropones. Increasing Smectic Thermal Stabilities by the Lateral Polar Carbonyl Group
- Sythetic Modification of Cotylenol. Synthesis of 3α-Cotylenyl Methyl Dithiocarbonates with Four Diastereomeric Glycol Moieties and Their Plant Growth Regulating Activity
- Total Synthesis of (-)-Cotylenol, a Fungal Metabolite Having a Leaf Growth Activity
- High-Pressure Diels-Alder Reaction between Buckminsterfullerene and Tropone
- Geometrical Isomerism of the Exocyclic C=C Bonds of Heptafulvene Derivatives. Steric and Electronic Effects on the Rotational Barrier
- High-Pressure Diels-Alder Reaction of Cyclooctatetraene with Dimethyl 1,4-Dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene2,3-dicarboxylate. Single Crystalline State Valence Isomerization of a syn-Tricyclo[4.2.0.0^]octane Derivative
- Concomitant Formation of Isomeric 1-, 2-, and 3-Substituted Heptafulvenes from 2-Substituted Tropones and Active Methylene Compounds
- Synthesis and Properties of 1-(Tropon-2-yl)-1-aza-4,7,10,13-tetraoxacyclopentadecanes. Preferential Complexation of Lithium Salt among the Alkali Salts
- Preferential Coordination of Mercury(II) Chloride to Ethereal Oxygens over Sulfurs in 23-Dicyanomethylene-5,8,11,14,17-pentaoxa-2,20-dithiabicyclo[19.4.1]hexacosa-1(26),21,24-triene and 20-Dicyanomethylene-5,8,11,14,-tetraoxa-2,17-dithiabicyclo[16.4.1]tri
- Construction of Functionalized Dolabellane Framework via the Stereocontrolled Cope Rearrangement of a 1,3,2-Dioxasilacycloheptane Derivative
- A Total Synthesis of (±)-Sativene via High-Pressure Diels-Alder Route
- One-pot Formation of Functionalized Cyclopentenone Derivatives via Retro-Benzilic Acid Rearrangement of the Proto-Photocycloadducts of Methy12,4-Dioxopentanoate to Methylenecycloalkanes
- Rose-Bengal-Sensitized Photooxidation of Quadricyclane. A [2σ+2σ+2π] Cycloaddition of Singlet Oxygen
- Chemistry of Azulenequinones and Their Analogues
- Preferential Exhibition of Smectic A Phase through Intramolecular Hydrogen Bonding in 2-Amino-5-phenyltropone Liquid Crystals
- Diels-Alder Reactions of Fullerene C_ and 4-Hydroxytropones
- Synthetic Photochemistry, LXVII.^ A Total Synthesis of (±)-Hinesol and (±)-Agarospirol via retro-Benzilic Acid Rearrangement
- Crystal Structures of 9, 10-Bis[bis(2-pyridylmethy)aminomethyl]anthracene and Its ZnCl_2 Complex. Intramolecular π-π Interaction between Anthracene and ZnCl_2-complexed Pyridine
- PB71 SYNTHESIS OF 5-8-5-MEMBERED TRICYCLIC TERPENOIDS AND THEIR B-SECO-RELATED COMPOUNDS
- Troponoid Liquid Crystals(Abstract from International Seminar on Manufacturing of Advanced Materials)
- Reactions of tetrasulfur tetranitride with tropolone and its several halogeno derivatives. Preparations of 4H-cyclohepta[c][1,2,5]thiadiazol-4-ones, 6H-cyclohepta[c][1,2,5]thiadiazol-6-one, and 7H-cyclohepta[1,2-c:3,4-c']bis[1,2,5]thiadiazol-7-ones.
- Synthetic photochemistry. XLV. Photoconversion of 2-methylenehomobarrelenes to 9-methylenebarbaralanes.
- High-pressure cycloaddition of tropones to ethoxyethene. An occurrence of (4+2) and (8+2) cycloadditions.
- Synthetic photochemistry. LIV. The photoaddition reaction of methyl 2,4-dioxopentanoate with 2,5-dimethyl-2,4-hexadiene, a sterically crowded conjugated diene.
- Synthetic photochemistry.LII. Substituent effects of a bromine atom on the high-pressure cycloaddition between 1-acetyl-7-bromocyclohepta[b]pyrrol-2(1H)-one and 2,3-bis(methoxycarbonyl)-7-oxanorbornadiene and the photorearrangement of 2-acetyl-9-bromo-2-a
- Synthetic photochemistry. XLVII. Formation and degenerate Cope rearrangement of 9-dicyanomethylenebarbaralane.
- Synthetic photochemistry. XLVI. Cycloaddition of exo, endo-2,7-bis-(methoxycarbonyl)-11,12-dioxatetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene and conjugated enones and p-quinones.
- The solid-phase 13C NMR spectra of several tropolone derivatives.
- Synthetic Photochemistry. LVII. Facile Photochemical Construction of Hexahydro-as-indacene Skeleton, a Carbon Framework of Ikarugamycin, from High-Pressure Diels-Alder Adducts of Tropones-Cyclopentenone.
- Synthetic photochemistry. XLII. Total synthesis of cycloaraneosene, a fundamental hydrocarbon of 5-8-5-membered tricyclic diterpenoid from Sordaria araneosa.
- The kinetic evidence of the concerted[1,9]sigmatropy for the acetyl migration in the 2-acetoxytropones. The NMR spectral analysis of the seven-fold degenerated acetotropy of hexaacetoxytropone.
- Superjacent and subjacent orbitals participations for kinetically-controlled cycloaddition reactions of 2H-cyclohepta[b]furan-2-ones and 8,8-dicyanoheptafulvene to 2,3-bis(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptadiene.
- Novel preparation of 1- and 3-substituted bicyclo[3.2.2]nona-3,6,8-trien-2-ones from tropones and 2,3-bis(methoxycarbonyl)-7-oxabicyclo-[2.2.1]heptadiene by high-pressure cycloaddition-thermal cycloreversion procedure.
- Pressure-accelerated Diels-Alder reactions of tropones with aromatic p-quinones.
- Synthetic photochemistry LV. Characterization of the lumiketone-type photoproducts, bicyclo(3.2.0)hept-3-en-2-ones, from 2,6-cycloheptadien-1-ones.
- Thermal cycloaddition reaction of tropone to 1,1-diethoxyethene. Structure revision of Cantrell's Diels-Alder adduct.
- The effect of pressure on sigmatropic rearrangements of seven-membered conjugated systems. [3, 3] And [1, 9]sigmatropies.