Restricted rotation involving the tetrahedral carbon. LV. Differential effects of the peri-substituents on the rotational barriers in 9-ethyl-,9-allyl-, and 9-benzyltriptycenes.

スポンサーリンク

概要

• 論文の詳細を見る

• Energy barriers to rotation about the bridgehead-to-substituent bond in 9-ethyl-, 9-allyl-, and 9-benzyltriptycene derivatives with varying degrees of <I>peri</I>-substitution were studied by dynamic NMR and in one case by the classical kinetic method. In the singly <I>peri</I>-substituted series (1,4-dimethoxy derivatives) the barrier decreases in the order of 9-ethyl>9-allyl>9-benzyl. In the doubly <I>peri</I>-substituted series (1,8-dichloro derivatives) the barriers are alike irrespective of the 9-substituent, and in the triply <I>peri</I>-substituted series (1,4-dimethyl-8,13-dichloro derivatives) the barrier decreases in the order of 9-benzyl>9-allyl>9-ethyl. The reversal of the trend on the change in <I>peri</I>-substitution patterns may be explained on the basis of the change in the interaction between the <I>peri</I>- and 9-substituents in both the ground and the transition states.

• 公益社団法人 日本化学会の論文

著者

• Yamamoto Gaku

  Department Of Chemistry Faculty Of Science The University Of Tokyo

• Oki Michinori

  Department Of Chemistry Faculty Of Science Okawama University Of Science

• Oki Michinori

  Department of Chemistry Faculty of Science, The University of Tokyo

関連論文

• Synthesis and Properties of Methano-Bridged Bisdehydro[17]-, -[19]-, -[21]- annulenones and the Related Compounds
• Synthesis and Properties of a Bismethano-bridged Bisdehydro[21]annulenone. Conformation in Solution and in the Crystalline State
• A Methano-Bridged Dehydro[24]annulenedione. A Highly Diatropic Dicationic 22π-Electron Species in D_2SO_4
• Reaction of 2-(Alkylthiomethyl)phenyllithium with Copper(I) Halides and Structure and Properties of One of the Products -Copper(I) Complexes of 2,2'-Bis(alkylthiomethyl)biphenyl^
• Catenation of 2,2'-Bis(ethylthiomethyl)biphenyl with Copper(I) Bromide
• Reactivitie of Stable Rotamers. XLII. Generation and Fates of Rotameric [1-(9-Fluorenyl)-2-naphthyl]methyl Radicals
• Reactivities of Stable Rotamers. XLI. Reactions of 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalene Rotamers with Chalcogenyl Halides and Observation of Coloration During the Reaction of Methanesulfenyl Chloride and the ap-Rotamer
• Reactions of ap- and sp- 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalene Rotamers with Bromine Chloride or Iodine Chloride and Unusual Populations of the Corresponding 1-(9-Fluorenyl)-2-[(E)-2-halo-1-methylethenyl]naphthalene Rotamers^
• Reactivities of Stable Rotamers. XXXVIII. Reaction of Chlorine with 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalene Rotamers : Outstanding Solvent Effects on Product Distribution and Ritter Type Reactions in Acetonitrile^
• Reactivities of Stable Rotamers. XLIII. Diazotization of 2-Methyl-2-(1,2,3,4-tetrachloro- and 1,4-dimethoxy-9-triptycyl)propylamine Rotamers^
• Reactivities of Stable Rotamers. XXXV. Diazotization of 2-(1,4-Dimethyl-9-triptycyl)-2-methyl-Propylamine Rotamers
• Effects of Molecular Association in the Radical-Cations of 1,8-Bis (ethylenedithiotetrathiafulvalenyl) naphthalene^1
• Absolute Conformation and Chiroptical Properties. VII. 9(1')-Msc and Psc Forms of 9-(2-Fluoro-1,1-dimethylethyl)-and 9-(1,1-Dimethylpropyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracenes
• Structural and Stereochemical Studies of Tris[2-(trifluoromethyl)phenyl]borane: Spontaneous Resolution, Stereodynamics, and Intramolecular C-F【triple bond】B Interactions
• Rotational Isomerism Involving an Acetylenic Carbon: Synthesis of and Barrier to Rotation around C(sp)-C(sp^3) Bonds in Bis(1,4-disubstituted 9-triptycyl)ethynes
• Absolute Conformation and Chiroptical Properties. VI. 2,2',3,3'-Tetramethoxy-9,9'-bitriptycyl : A Stereochemical Analog of 1,2-Disubstituted Ethane with Identical Substituents^
• Synthesis, Structure, and Reactions of the First Stable Aromatic S-Nitrosothiol Bearing a Novel Dendrimer-Type Steric Protection Group
• Static and Dynamic Stereochemistry of Tris(9-triptycyl)stannane Derivatives
• Dynamic Stereochemistry of Alkyltris(9-triptycyl)stannanes
• Deamination of 1-Alkyl-9-aminomethyltriptycenes : Participation of a Neighboring 1-Alkyl Substituent
• Synthesis and Structures of 9-Triptycylallene Derivatives
• Synthesis and Stereochemistry of N-Phenyl-N-9-triptycylhydroxylamine Derivatives and Related Compounds
• Static and Dynamic Stereochemistry of N-(1,4-Dimethyl-9-triptycyl)-hydroxylamine Derivatives
• Static and Dynamic Stereochemistry of O-Substituted N-9-Triptycylhydroxylamines
• A Report From the Steering Group of the Special Project Research on Science Education
• ラット胃・十二指腸液逆流モデルを用いて検討した呼吸器疾患と微量誤嚥との関連性の組織学的検討
• Nickel-Catalyzed Dimerization of [5]Cumulenes (Hexapentaenes)
• Dimensiosolvatic Effects. VI. Rates of Ionization of 2-Fluoro-4, 4, 5, 5-tetramethyl-1, 3-dioxolane : Dimensiosolvatic vs. Hydrogen-Bond Effects
• Dimensiosolvatic Effects. IV. Topomerization in Alkyl α-Chlorobenzyl Ethers and Insights into Mechanisms of Their Thermolyses^
• Dimensiosolvatic Effects. III. Quantification of Dimensiosolvatic Effects by Solvolyses of 2-Bromoadamantane in Water-Alcohol Mixtures^
• Effects of Solvent Molecular Size on Rates of Topomerization in Organolithium Compounds
• Reactivities of Stable Rotamers. XXXIX. Thermal Decomposition of t-Butyl 3-Methyl-3-(substituted 9-triptycyl)peroxybutanoate Rotamers^
• High animal-fat intake changes the bile-acid composition of bile juice and enhances the development of Barrett's esophagus and esophageal adenocarcinoma in a rat duodenal-contents reflux model
• Bromine Adducts of 9,10-Diheteratriptycene Derivatives
• Static and Dynamic Stereochemistry of N-(9-Triptycyl)acetanilde
• Stereochemistry of N-Ethyl-N-9-triptycylhydroxylamine and Its O-Alkyl Derivatives
• Deamination of 1-Alkyl-9-aminomethyltriptycenes : Participation of the α-C-H Bond of the 1-Alkyl Group
• Structures and Stereodynamics of N-9-Triptycylacetamide and Its N-Alkyl Derivatives
• Dynamic Stereochemistry of N-Phenyl-9-triptycylamine and Its N-Alkyl Derivatives^#
• Structures and Tropicity of Hydrogenation Products of a Bisdehydro[13]annulenone and a Bisdehydro[15]annulenone
• Structure and Stereodynamics of N-Ethyl-N-9-triptycylacetamide: Co-existence of Z- and E-Isomers in a Single Crystal and Pyramidal Amide Nitrogen Both in Crystal and in Solution
• Structure and Stereodynamics of N-Methyl-N-9-triptycylacetamide : Pyramidal Amide Nitrogen in the Crystalline State
• Stereodynamics of N-Phenyl-9-triptycylamine as a Gear-rotation System
• Absolute Conformation of Methyl 3-(1,4-Dimethoxy- and 1,4-dimethyl-9-triptycyl)-3-methylbutanoate Rotamers
• The Synthesis of a [13][15]Fulvalene Derivative
• Static and Dynamic Stereochemistry of N-Alkyl-and N, O-Dialkyl-N-9-triptycylhydroxylamine Derivatives
• How Do Ethane-Type Molecules Avoid Eclipsing When Forced as Such? The Case of 7, 8, 9, 10-Tetrachloro-1, 1-dimethyl-1, 2, 6, 10b-tetrahydro-6, 10b-o-benzenoaceanthrylene
• School Systems and Chemical Education in Japan
• University Chemical Education in Japan : Its General Background
• Rotational Isomerism Involving an Acetylenic Carbon II : Effect of 1-Halogen Substituents on Rotamer Population and Rotational Barrier around C(sp)-C(sp^3) Bonds in Bis(9-triptycyl)ethynes^1
• Synthesis and Structure of 1,4-Dimethoxy and 1,4-Dimethyl-9-(trifluoromethyl)triptycenes
• A Bromine Adduct of 2, 3, 6, 7, 14, 15-Hexamethyl-9, 10-distibatriptycene. The First Stibonium-Stiborate Zwitterion
• Stereodynamics of N-Benzyl-N-methyl-9-aminotriptycene
• Synthesis and ^1H NMR Spectral Behavior of a Methano[20]annulenedione Derivative
• Syntheses of Novel Cyclic Undecapeptides Related to Gramicidin S with D-Phe-X-Pro Sequences
• Benzene-Ethene Interactions as Studied by ab initio Calculations
• Structure and Stereodynamics of N-9-Triptycyl-O-phenylhydroxylamine, an Unusual Product by the Reaction of 9-Nitrosotriptycene and Phenyllithium
• Effects of Solvent Molecular Size on Dissociation Rates of the N-H Bond in Ammonium Salts Derived from Tertiary Amines
• Synthesis and Properties of Trispiro[truxenetris(cycloalkane)]s
• Reactivities of Stable Rotamers XXXVII : Thermolyses and Photolyses of 2(1H)-Thioxo-1-pyridyl 3-(1, 4-Dimethyl-9-triptycyl)-3-methylbutanoate Rotamers^
• Mechanism of Sulfur Inversion in Sulfide Complexes of Gold(I) and Gold(III)
• Restricted Rotation Involving the Tetrahedral Carbon. LXIV. Barriers to Rotation of s-Alkyl Groups in 9-s-Alkyl-8,13-difluoro-1,4-dimethyl-and 1,2,3,4-tetrachloro-triptycenes
• Restricted Rotation Involving the Tetrahedral Carbon. LXIII. Endeavor toward Enhancing the Rotational Barrier in 9-s-Alkyltriptycenes^
• ラット胃・十二指腸液逆流モデルを用いて検討した呼吸器疾患と微量誤嚥との関連性の組織学的検討
• Enantiomeric Resolution and Absolute Stereochemistry of Stable Rotamers of Dimethyl 6,6'-Dimethyl-9,9'-bitriptycyl-2,2'-dicarboxylate as a Stereochemical Analog of (R^*,R^*)- and (R,S)-Tartaric Acids
• Literacy in Science and Technology
• Social Goals and Science Education in Japan
• Environmental Problems in General
• Reactivities of stable rotamers. XXII. Lewis acid-catalyzed reactions of 3-(1,4-disubstituted 9-triptycyl)-3-methylbutanoyl chloride. Isolation of rotameric ketones and competition between cyclizations to substituted and to unsubstituted benzene rings.
• Dynamic NMR as a nondestructive method for the determination of rates of dissociation. V. Proton affinities of p-substituted N,N-dibenzylanilines in aprotic solvents.
• Restricted Rotation Involving the Tetrahedral Carbon. XIV. Conformational Equilibria and Attractive Interactions in Substituted 9-Benzyltriptycenes
• Restricted Rotation Involving the Tetrahedral Carbon. XI. Barriers to Rotation and Conformational Preferences of Substituted 9-Isopropyltriptycenes
• Restricted rotation involving the tetrahedral carbon. XLII. Barriers to rotation and populations of rotamers in 9-(2-(substituted methyl)-1-napthyl)fluorenes.
• Reactivities of stable rotamers. XI. Rotamer distributions and some addition reactions to the carbonyl in 9-(2-(substituted carbonyl)-1-naphthyl)fluorene rotamers.
• Reactivities of stable rotamers. X. Reactions of 9-(2-formyl-1-naphthyl)fluorene rotamers and related compounds.
• Dynamic NMR as a nondestructive method for the determination of rates of dissociation. III. Ionic dissociation of .ALPHA.-chlorodibenzyl sulfide.
• Reaction of trans-Stilbene with Methanesulfenyl Chloride
• Reactivities of stable rotamers. VI. Manifestation of differential reactivities of the methyls in a t-butyl group in radical halogenations.
• Restricted rotation involving the tetrahedral carbon. XLIII. Buttressing effect on rotational barriers in bromine-substituted 9-(2-methoxy-4,6-dimethylphenyl)fluorenes.
• Anomeric Effect Involving Carboxyl and Ethynyl Group in Sulfur-Containing Heterocycles
• 2-Chloro-1,3,5-trithiane and 2-chloro-1,3-dithiane. Their ionic dissociation and reactions with nucleophiles.
• Direct measurement of the rates of ionic dissociation by dynamic NMR technique. Dissociation of .ALPHA.-chlorodibenzyl sulfides.
• Dynamic NMR as a nondestructive method for the determination of rates of dissociation. XII. Dissociation of the olefin in trans-dichloro(4-methyl-1-pentene)(4-substituted pyridine 1-oxide)platinum(II) complexes.
• Rotamer populations and molecular structure of 9-isobutyl-1,4-dimethoxytriptvcene: Further evidence for the presence of CH3...O hydrogen bond.
• Dynamic NMR as a Nondestructive Method for the Determination of Rates of Dissociation. XVIII. Factors Affecting the Rates of Dissociation of N-B Bond in the Coordinated Form of 9-(2-(Dialkylaminomethyl)-phenyl)-9-borabicyclo(3.3.1)nonanes.
• Dynamic NMR as a nondestructive method for the determination of rates of dissociation. XVII. Dissociation of the N-B bond in the coordinated form of 2-(2-(dimethylaminomethyl)phenyl)-4,4-diphenyl-1,3,2-dioxaborolane and related compounds.
• Reactivities of stable rotamers. XII. Reactions of 9-(2-bromomethyl-6-methylphenyl)fluorene rotamers with nucleophiles.
• Restricted rotation involving the tetrahedral carbon. XXXIX. 9-(2-Methoxy-1-methylethyl)triptycene derivatives.
• Effects of para-Substituents on the Rates of Inversion of Biphenyl Derivatives. I. 5,7-Dihydrodibenzo[c,e]thiepins
• Restricted rotation involving the tetrahedral carbon. LIX Stereodynamics of singly peri-substituted 9-(3,5-dimethylphenoxy)triptycene derivatives.
• Restricted rotation involving the tetrahedral carbon. LII. Rotational barriers in 1,2,3,4-tetrafluoro- and 1,4-dimethoxy-9-(1-cyano-1-methylethyl)triptycenes.
• Reactivities of stable rotamers. VIII. Difference in reactivities of 1,2,3,4-tetrachloro-9-(2-halo-1,1-dimethylethyl)triptycene rotamers in Lewis acid-catalyzed reactions.
• Nuclear Magnetic Resonance Study of the Effect of the Hydrogen Bond on the Internal Rotation of Biphenyls
• Restricted rotation involving the tetrahedral carbon. LV. Differential effects of the peri-substituents on the rotational barriers in 9-ethyl-,9-allyl-, and 9-benzyltriptycenes.
• Attractive interactions between carbonyls and groups bearing lone-pair electrons in triptycene systems.
• Restricted rotation involving the tetrahedral carbon. L. Rotamer distributions and rotational barriers in some 9-(1-methoxyethyl)triptycene derivatives.
• CH3...O Hydrogen bond. Implications of its presence from the substituent effects on the populations of rotamers in 4-substituted 9-ethyl-l-methoxytriptycenes and 9-(substituted phenoxymethyl)-1,4-dimethyltriptycenes.
• Restricted rotation involving the tetrahedral carbon. XLIV. Atropisomers of 2,3-dichloro-9-(1-hydroxy-1-methylethyl)-triptycene and related compounds.
• Reactivities of stable rotamers. XXIV. Formation of isomeric ketones by cyclization of rotameric 3-methyl-3-(1,2,3,4-tetrahalo-9-triptycyl)butanoyl chloride and barriers to isomerization of the ketones.
• Restricted rotation involving the tetrahedral carbon. XXXI. Barriers to rotation in 2,3-dichloro-9-(1-cyano or 1-methoxycarbonyl-1-methylethyl)triptycenes.

もっと見る 閉じる

スポンサーリンク