Thermolysis and Photolysis of Benzopinacol Dicarboxylates

スポンサーリンク

概要

• 論文の詳細を見る

• Thermal decomposition of benzopinacol dicarboxylates (I) results in the cleavage of the central carbon-carbon bond to afford benzhydryl esters (II) and benzophenone (III). Benzopinacol diacetate (Ia) in benzyl alcohol-benzene solution produces benzyl acetate <I>via</I> ionic reaction path, whereas Ia in THF-benzene or in toluene gives radical products such as 2-diphenylmethylenetetrahydrofuran and bibenzyl, respectively. Photolysis of I proceeds in the similar manner as thermolysis to afford II and III. The ester II is further decarboxylated photo-chemically to give 1,1-diphenylalkane, diphenylmethane, and 1,1,2,2-tetraphenylethane. The photochemical solvent incorporation of II proceeds in both radical and ionic sense. Such dual nature of the reaction products in thermolysis and photolysis of I and of the photodecarboxylation of II is explained in terms of the intimate ion-radical pair hypothesis proposed by Walling.

• 公益社団法人 日本化学会の論文

著者

• Yamamoto Yasusi

  Department Of Biology Faculty Of Science Kyushu University

• Nozaki Hitosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Shirafuji Tamio

  Department of Industrial Chemistry, Kyoto University

関連論文

• 海外留学研究報告 Identification of ligands for functional Mn in the photosynthetic water-oxidizing complex.--An approach by combined techniques of photoactivation and chemical modification with amino group-labeling reagents
• Two Plastoquinone A Molecules Are Required for Photosystem II Activity : Analysis in Hexane-Extracted Photosystem II Particles
• Electrostatic Interaction between Plastocyanin and P700 in the Electron Transfer Reaction of Photosystem I-Enriched Particles
• Characteristics of light-induced 515-nm absorbance change in spinach chloroplasts at lower temperatures II. Relationship between 515-nm absorbance change and rapid H^+ uptake in chloroplasts after a short flash illumination
• ASSEMBLY OF OXYGEN EVOLVING SUBUNITS IN PHOTOSYSTEM II
• Analysis of photosystem II using particle II preparation II. Action spectra for Hill activities and fluorescence properties of variously-treated particle II preparations
• Discrimination and characterization of photosystem I-and photosystem II-induced 515-nm absorbance changes in chloroplasts II. Separate local fields in thylakoids indicated by differential responses of the 515-nm absorbance change
• Analysis of photosystem II using particle II preparation. I. Experimental evidence supporting the idea of the involvement of two light reactions in photosystem II of green plant photosynthesis
• Characteristics of light-induced H^+ transport in spinach chloroplast at lower temperatures II. A possible role of structured water in H^+ transport of chloroplast near 0℃
• Relationship between the Stability of Antenna Chl a-Binding Proteins CP43/47 and the Accumulation of the Extrinsic 30-kDa Protein in PS II in Euglena
• Characteristics of light-induced 515-nm absorbance change in spinach chloroplasts at lower temperatures I. Participation of structural changes of thylakoid membranes in light-induced 515-nm absorbance change
• Characteristics of light-induced H^+ transport in spinach chloroplast at lower temperatures I. Relationship between H^+ transport and physical changes of the microenvironment in chloroplast membranes
• Discrimination and characterization of photosystem I and photosystem II-induced 515-nm absorbance change in chloroplasts I. Dissipation of electric field and related processes
• Quality Control of Photosystem II
• Thiocarbonyl Ylides. Attempted Preparation and Related Reactions
• Preparative and Structural Studies of Kostanecki's Compound
• The Reduction of gem-Dibromocyclopropanes by Means of Chromium(II) Acetate or Potassium Pentacyanocobaltate
• Regiocontrolled formation of 4,5-dihydro-3(2H)-furanones from 2-butyne-1,4-diol derivatives. Synthesis of bullatenone and geiparvarin.
• Highly selective carbon-carbon bond forming reactions mediated by chromium(II) reagents.
• Cross-coupling reaction between enol phosphates and organoaluminium compounds in the presence of palladium(0) catalyst.
• The Reaction of Styryl Sulfoxides or Sulfones with Boranes
• Reaction of organoaluminium reagents with cyclopropylmethyl acetates and 2-vinylcyclopropane-1,1-dicarboxylate esters.
• 1-Bromo-2-ethoxycyclopropyllithium: A synthetic equivalent of 2-lithio- or 3-lithiopropenal. Application to the synthesis of juvenile hormone (JH-II), .BETA.-sinensal, and jasmonoids.
• A novel synthesis of .ALPHA.-methylene-.GAMMA.-butyrolactones.
• Isomerization of allylic alcohols catalyzed by vanadium or molybdenum complexes.
• Reformatsky type reaction with new aluminium reagents containing Al-Sn or Al-Pb linkage.
• New methods for the synthesis of 3(2H)-furanones and 2(5H)-furanones.
• Alkylation of bromocyclopropanes and bromoarenes by means of dibutylcopperlithium and alkyl halides.
• A facile ring enlargement reaction via .BETA.-oxido carbenoid.
• The Reaction of Ethyl Azidoformate with Electron Deficient Olefins and the Thermal Ring Opening of the Resulting Aziridines.
• The Photolysis and Thermolysis of Ethyl Azidoformate in the Presence of Ketones
• A practical synthesis of polyhalomethyllithium-carbonyl adducts.
• Abnormal nazarov reaction. A new synthetic approach to 2,3-disubstituted 2-cyclopentenones.
• Tungsten hexachloride-catalyzed decomposition of diazo compounds. A novel oxazole synthesis.
• Condensation Reactions of Sulfonylcarbanion
• Synthesis and Reactions of Sulfonium Diacylmethylide Having Active Hydrogen
• Intramolecular cyclization of nerol and the related attack of (Z)-allylic alcohol moiety on the terminal olefin linkage as induced by TiCl4-PhNHMe complex. Synthesis of nezukone.
• The Nucleophilic Cyclopropylation of the Condensed Aromatic Ring with Sulf onylcarbanion
• Stereochemical studies on the nucleophilic substitution in the reaction of allylic phosphates with organoaluminum reagents.
• Synthesis of [9]Heterophanes from 2-Cyclododecenone
• Carbocyclic ring formation by the intramolecular reaction between enol silyl ether and allylic acetate moieties.
• Synthesis of homoallylic alcohols from allylic phosphates and aldehydes with organoaluminum reagent containing Al-Sn linkage.
• The 1-Methylene Derivatives of [7](2,6)Pyridinophane. Preparative and Conformational Studies
• The Absolute Configurations of 2-Phenylaziridine and Its Derivatives
• Thermolysis and Photolysis of Benzopinacol Dicarboxylates
• The Reaction of O,O′-Diethyl α-Lithiomethylphosphonate with Organic Dihalides
• The Oxidation of Alkylbenzenes and Acylcarbinols by Means of Benzopinacol Diesters
• Cyclopentenone synthesis from 1,1-dichloroallyllithium-ketone adducts as well as from dichlorocarbene-allyl alcohol adducts.
• The Dehalogenation of Organic Halides by Means of Iron(II) Chloride in Dimethyl Sulfoxide
• Rearrangement of vic-diol monoacetates promoted by organoaluminium compounds.
• Stereoselective epoxidation of allylic alcohols and dehydrogenative oxidation of secondary alcohols by means of t-butyl hydroperoxide and aluminium reagents.
• Baeyer-Villiger oxidation with Me3SiOOSiMe3 under assistance of SnCl4 or BF3OEt2.
• Chromium(VI) or ruthenium(II) complex catalysis in oxidation of alcohols to aldehydes and ketones by means of bis(trimethylsilyl) peroxide.
• Aliphatic Claisen rearrangement promoted by organoaluminium reagents.
• The Syntheses and Reactions of Sulfenyl-substituted Sulfonium Ylides
• The Acid-Catalyzed Ring-Opening of Cyclooctenimine Derivatives
• Cr(III) or Ce(IV) impregnated perfluorinated resin-sulfonic acid catalyst for the oxidation of alcohols.
• A New Synthesis of Thiophenes
• Photoinduced Transannular Reaction of 4,5-Octamethylene-1,3-dioxolen-2-one
• The Reaction of Acyl-substituted Sulfonium and Pyridinium Ylides with Diphenylthiirene Dioxide
• Palladium-catalyzed ketone synthesis from acyl chloride and organoaluminum reagents.
• Preparation of 2-alkenylsilanes and 2-alkenylstannanes by the reaction of 2-alkenyl-1,1-cyclopropanedicarboxylate esters with PhMe2SiAlEt2 and (Ph3Sn)2Zn. Generation of 2-alkenyl-3-cyclopentene-1,1-decarboxylates via alkenyl-substituted .PI.-allylpalladiu
• Photochemistry of Non-enolizable β-Diketones Containing Cyclopropane Ring in Conjugation

もっと見る 閉じる

スポンサーリンク