Photoadducts of 4,6-dimethyl-and 4-methoxy-6-methyl-2-pyrones with chloroethylenes and their dehydrochlorination.
スポンサーリンク
概要
- 論文の詳細を見る
Sensitized photoreactions of 2-pyrones with chloroethylenes gave two kinds of [2+2]cycloadducts, 2-oxabicyclo[4.2.0]oct-4-en-3-ones (<B>4</B>, <B>8</B>) and across the C<SUB>3</SUB>–C<SUB>4</SUB> double bond in 2-pyrone, benzene derivatives, and/or cyclobutanecarboxylic acids: Their relative yields greatly depended upon the nature of the reactants. The dehydrochlorination of the cycloadducts <B>4</B> and <B>8</B> across the C<SUB>5</SUB>–C<SUB>6</SUB> double bonds in the pyrones with triethylamine in ethanol gave 5-ethenyl-2-pyrones, whose structures were previously incorrectly assigned as oxocinones, via a symmetry-allowed ring opening of 2-oxabicyclo[4.2.0]octa-4,6-dien-3-ones. Some 5-ethenyl-2-pyrones possessing a chlorinated ethenyl group finally affords 5-ethynyl-2-pyrones by an anti-elimination of hydrogen chloride. The X-ray crystallographic analyses of 5-ethenyl- and 5-ethynyl-2-pyrones are also described.
- 公益社団法人 日本化学会の論文
著者
-
Imada Kiyohisa
Department Of Applied Chemistry Faculty Of Engineering Miyazaki University
-
Shimo Tetsuro
Department Of Applied Chemistry And Chemical Engineering Faculty Of Engineering Kagoshima University
-
Somekawa Kenichi
Department Of Applied Chemistry And Chemical Engineering Faculty Of Engineering Kagoshima University
-
Tsuge Otohiko
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences Kyushu University
-
Tanabe Kimiko
Department of Industrial Chemistry, Faculty of Engineering, Miyazaki University
-
Wakikawa Yusuke
Department of Applied Chemistry, Faculty of Engineering, Kagoshima University
-
Uemura Hisako
Department of Applied Chemistry, Faculty of Engineering, Kagoshima University
関連論文
- ルピニン誘導体のX線結晶構造解析
- 水素化ホウ素ナトリウム還元による5-アセトキシ-または5-ベンゾイルオキシ-4-クロマノン類から5-クロマノ-ル類の合成
- Cell-bound Pullulanase from Streptomyces sp. No.27
- Maltotetraose-producing Amylase from Bacillus sp. MG-4(Biological Chemistry)
- Maltotriose-producing Amylase from Microbacterium imperiale(Microbiology & Fermentation Industry)
- 728 Aureobasidium属菌の生産するβ-キシロシダーゼの精製と性質
- 726 耐酸性及び耐熱性に優れたβ-グルコシダーゼの酵素特性
- 201 耐酸性通性嫌気性細菌による水素生産
- フィブリル化性の異なる再生セルロース繊維の酵素処理による構造解析
- アルギン酸塩を媒体とした卵膜分散体の作製方法とその物質透過特性 (I) アルギン酸バリウムとスケトウダラ卵膜の分散体
- 偏光顕微鏡法による干渉色を利用した再生セルロース中空糸の微細構造の評価
- 複屈折率測定から評価した再生セルロース固体の超分子構造の経時変化
- セルロース固体の形態複屈折率の評価
- Crystal Structure of 9-[trans-3′, 4′-Di(benzyloxymethyl)-cyclopropylidenemethylenyl]adenine
- Crystal Structure of 1 : 1 Complex Crystal between 4-(3-Methoxybenzyloxy)-6-methyl-2-pyrone and Maleimide
- Crystal Structure of 1 : 1 Complex Crystal between 4-(3-Methoxybenzyloxy)-6-methyl-2-pyrone and Maleimide
- Stabilities of The Deglycosylated Aspergillus β-Fructofuranosidase
- 325 Aureobasidium属菌の生産するβ-グルコシダーゼの精製と性質
- Production,purification and properties of the Aspergillus β-fructofuranosidase
- Microbacterium imperialeの生産するマルトトリオース生成酵素によるデンプン糖化条件
- Acid-Stable and Thermostable α-Amylase from Bacillus licheniformis α
- 結晶セルロース粒子の配向性が圧縮成形特性に及ぼす影響
- 機能を持つ多孔質ガラス
- 多孔質ガラスの表面状態とその化学修飾
- 多孔質ガラス上での核酸の合成
- 多孔質ガラスの表面状態と細孔内表面の化学修飾
- ポリエチレン単結晶の溶液結晶化における周辺薄層の発生
- Formation of 4-Hydroxy-3-(oxan-3-yl)coumarin from Photochemical Reaction between 4-Hydroxycoumarin and 3,4-Dihydro-2H-pyran and MO Analysis
- Solid-State Photocycloaddition of 6,6'-Dimethyl-4,4'-polymethylenedioxy-di-2-pyrones to Benzophenone
- Crystal Structures of 4-Methoxy-6-methyl-and 4-Hydroxy-6methyl-2-pyrones
- Crystal Structure of 4,13-Dimethyl-3,7,10,14,19,22,25-heptaoxapentacyclo-[25.0.0^.0^.0^.0^]heptacosa-4,11-diene-2,15-dione
- Preferred Head-to-tail Adduct in the Solid-state [2+2] Photodimerization of 2, 5-Dimethyl-4-hydroxy-3(2H)-furanone
- EFFECT OF SUBSTITUENTS ON ETHYLENE BACKBONE UPON REDOX POTENTIAL OF [Cu(salen)] HOMOLOGS
- Enzymatic Production of D-Mannose from D-Fructose by Mannose Isomerase
- The Effect of Deglycosylation on the Activity of Glucosyltransferase from Aureobasidium
- Immobilization of β-fructofuranosidase from aspergillus japonicus on DEAE-cellulose
- Immobilization of a Fructosyl-Transferring Enzyme from Aureobasidium sp. : on Shirasu Porous Glass
- Crystal Structure of Methyl endo-8-Cyano-exo-8-methyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-6-carboxylate
- Molecular simulation of enantiodifferentiating photoisomerization of cyclooctene by chiral sensitizers (特集 計算化学アプリケーションによる生命・物質科学の探求)
- A Gene Encoding Endo-1, 4-β-glucanase from Bacillus sp. 22-28
- Protein and Starch in Tubers of Winged Bean, Psophocarpus tetragonolobus(L.) DC., and Yam Bean, Pachyrrhizus erosus(L.)Urban
- Protein and Trypsin Inhibitor in Immature Pods of Winged Bean, Psophocarpus tetragonolobus (L.)DC.
- Molecular Simulations of Photoaddition Selectivity and Chirality in Challenging Photochemical Reactions
- Origin of the Endo/Exo Stereoselectivity and Syn/Anti Face-Selectivity in Diels-Alder Reactions, Determined by Transition State Energy Partitioning
- Origin of Regioselectivity in Photocycloaddition Reactions of 2-Cyclohexenone with Cycloalkenecarboxylates
- Conformation of an Arabinoxylan Isolated from the Rice Endosperm Cell Wall by X-Ray Diffraction and a Conformational Analysis
- 多糖類の利用--機能性の発現に向けて
- X線回折による多糖構造の解析
- 多糖類の応用 (粘着の世界)
- ベンズアミド類の13C NMR化学シフトにおける置換基効果の加成性
- New Synthetic Route to 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines through Photoamination of 5-Alkoxy- and 5-Hydroxy-5H-dibenzo[a,d]cycloheptenes Followed by a Transannular Reaction with Acetic Acid
- Amination of o-Alkenylphenols with Alkylamines via Photoinduced Proton Transfer
- Peri-, Site- and Stereocontrolled Photocycloaddition of 4-Methoxy-6-methyl-2-pyrone with Maleimide Induced by the Hydrogen Bond and CT Stacking in the Solid State
- Crystal Structure of Photocycloadduct between 4-Methoxy-6-methyl-2-pyrone and Maleimide
- Synthesis of a Carbocyclic Oxetanociu Using Photocycloaddition
- Studies of N-Sulfinyl Compounds. IV. The Reactions of N-Sulfinylanilines and -phenylhydrazines with Styrene Oxide
- Synthesis of hexahydroindenones through a Diels-Alder cycloaddition and Nazarov cyclization sequence of triene alcohols.
- Stereoselective cycloadditions of pyridinium or isoquinolinium methylides with olefinic dipolarophiles and subsequent cycloadditions of the cycloadducts with nitrile oxides.
- Synthesis of 5,8-dihydroxy-2-methoxy-1,4-naphthoquinone derivatives. A major naphthoquinone moiety of some of naphthoquinone antibiotics.
- Organic photochemical reactions. XXXI. Photosensitized ring-cleavage reactions of 2,2-diaryloxetanes by aromatic nitriles.
- Photoadducts of 4,6-dimethyl-and 4-methoxy-6-methyl-2-pyrones with chloroethylenes and their dehydrochlorination.
- Molecular structures of diarylcyclobutanes associated with reactivities in ring-cleavage reactions: Implications of conformationally controlled through-bond coupling.
- The crystal structure of 11-(p-bromophenyl)-11-cyano-12-phenyl-6b-(1-pyrrolidinyl)-6b,6c,11,12a-tetrahydroindeno(1'2':3,4)-cyclopenta(1,2-a)acenaphthylene acetone solvate.
- Isolation and Structure of a New Metabolite of Pyridoxine in Seedlings of Pisum sativum L.
- Nucleophilic aminomethylation of aldehydes with .ALPHA.-amino alkylsilanes.
- Photoadducts of 2-pyridones with chloroethylenes and their derivatives.
- The reaction of 1-(1-pyrrolidinyl)acenaphthylene with electrophilic acetylenes.
- Studies of Compounds Related to Azines. VII. The Pyrorlysis of 2-Acetylthiophene- and 2-Acetylfuranketazine
- Photochemistry of heterocyclic compounds. VII. Photochemical reaction of 2,5-diphenyl-1,3,4-oxadiazole with benzo[b]thiophenes.
- Synthetic versatility of N-(silylmethyl)imines : Water-induced generation of N-protonated azomethine ylides of nonstabilized type and fluoride-induced generation of 2-azaallyl anions.
- Reactions of 1,4-bis(trimethylsilyl)-1,4-dihydropyridines with carbonyl compounds : A new method for regioselective synthesis of 3-alkylpyridines.
- Stereochemical study on 1,3-dipolar cycloaddition reactions of heteroaromatic N-ylides with symmetrically substituted cis and trans olefins.
- Double cycloaddition reaction of imidazolium methylides. Intermolecular 1,3-dipolar and intramolecular Diels-Alder cycloaddition reactions.
- A convenient route to 2-lithio-1,3-butadiene from chloroprene via 2-stannyl-1,3-butadiene.
- A Diels-Alder cycloaddition and electrocyclization sequence as a new (6.5) annelation method to benzene ring.
- Cross diene-transmissive Diels-Alder cycloaddition reaction of bis(silyloxy) cross-conjugated trienes.
- Studies of Acenaphthene Derivatives. XX. The Reactions of Benzylideneacenaphthenones with Sulfonium Ylides
- Synthesis of vinylcyclopropanes, cyclopropyl vinyl ketones, and 3-pyrazolyl vinyl ketones from 1-diazo-3-trimethylsilylpropanone.
- Reactions of trimethylsilyl cyanide and N-(trimethylsilyl)diphenylmethyleneamine with nitrones and thermal decompositions of their adducts.
- Studies of Acyl and Thioacyl Isocyanates. VIII. Cycloaddition Reactions of Benzoyl and Thiobenzoyl Isocyanates with Carbodiimides
- Compounds Related to Acridine. VIII. Reaction of 9-Vinylacridine with p-Substituted Nitrosobenzenes
- Diene-transmissive Diels-Alder reaction using 2-ethoxy-3-methylene-1,4-pentadiene and 2-(2-bromo-1-ethoxyethyl)-1,3-butadiene.
- Studies of N-Sulfinyl Compounds. VI. The Preparation of N-Sulfinylbenzamide and Its Reaction with Styrene Oxide
- Diene-transmissive Diels-Alder cycloaddition reaction of bis(silyloxy) cross-conjugated trienes.
- Compounds Related to Acridine. VII. The Synthesis of 9-Ethynylacridine and Its Reaction with p-Nitrosodialkylaniline
- Cycloaddition of pyridinium methylides with electron-deficient olefins and silica-gel mediated elimination of pyridines from the cycloadducts : A new method of alkylation or hydroalkylidenation of olefins.
- Synthesis of imido-substituted 3,8-diphenyl-1,2-diazacycloocta-2,4,6,8-tetraenes and their thermolysis.
- 1,3-Dipolar cycloadditions to 2-phenyl-1-azaspiro[2.2]pent-1-ene.
- Preparation of arylsulfonyl-substituted 3,8-diphenyl-1,2-diazacycloocta-2,4,6,8-tetraenes and their thermolysis.
- Studies of Acyl and Thioacyl Isocyanates. X. The Cycloaddition Reaction of Benzoyl and Thiobenzoyl Isocyanates with Benzaldazines
- Studies of Benzoylsulfene. IV. The Cycloaddition Reactions of Benzoylsulfene with Cinnamylideneamines