Journal of Synthetic Organic Chemistry, Japan

Chemistry of Single-atom Peri-bridged Naphthalenes

Juzo NAKAYAMA

1981Volume 39Issue 8 Pages 682-689
Published: August 01, 1981
Released on J-STAGE: January 22, 2010

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.39.682

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Single-atom peri-bridged naphthalenes are compounds in which the 1-and 8-carbon atoms of a naphthalene ring are bonded to a single atom in a bridging group (Z), forming a four-membered ring. The present review is concerned with the synthesis, structure, and reaction of this highly-strained unique ring system.

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The Chemistry of Aza-azulenes

Masaru KIMURA

1981Volume 39Issue 8 Pages 690-700
Published: August 01, 1981
Released on J-STAGE: January 22, 2010

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.39.690

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Detailed information about the similarities and differences in the behaviour of azulene and aza-azulenes is desirable for an experimental support of quantum chemical predictions as well as for the development of new tools for the synthesis of heterocycles. We would like to focus on the synthesis of aza-azulenes containing one or two nitrogen atoms in the five-membered ring or in the seven-membered ring, and further the cycloaddition of azulene and aza-azulenes with dienophiles.

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Prediction of Directional Selectivity of Photoreactions by Molecular Orbital Theory

Photochemically Induced Electrocyclization in Cycloheptatrienes

Takahiro TEZUKA, Osamu KIKUCHI, K. N. HOUK

1981Volume 39Issue 8 Pages 701-711
Published: August 01, 1981
Released on J-STAGE: January 22, 2010

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.39.701

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Several attempts to predict directional selectivity of photoreactions on the basis of molecular orbital theory are described. Particularly, attention is paid to predict regioselectivity and periselectivity of 1, 7 sigmatropic shifts and electrocyclizations of singlet state of cycloheptatrienes by our new indices ΔG_r, _s ΔE_r, _s' and/or sudden polarization model, and to show how our new prediction model (T-K-H model) is applicable for organic chemists. In addition to our own works, several static indices and models for predicting photoreactive sites, which include ΔP_r, _s', π-electron density, second order perturbation energy in the excited states, and Brember's empirical model, are also introduced.

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Photochemistry of Pyridinecarboxylic Acid Derivatives

Multiple Paths for Photoreactions and Simultaneous Contribution of Several Kinds of Excited States

Akira SUGIMORI

1981Volume 39Issue 8 Pages 712-722
Published: August 01, 1981
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.39.712

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Derivatives of pyridinecarboxylic acid show manifold photoreactivity depending on the reaction conditions. Some features of their photoreactions are : 1) Coexistence of ionic and radical reactions, 2) multiple paths for photoreactions (photo-alkylation of 3-pyridinecarboxylic ester in alcoholic solutions occurs via 4 different paths), 3) Simultaneous contribution of several excited states of the same multiplicity.

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Extension of Reactions of Activated Carboxylic Acid Derivatives to Polymer Syntheses

Syntheses of Polyamides and Their Analogs by Ring-Opening Polyaddition Reactions

Yoshio IMAI, Mitsuru UEDA

1981Volume 39Issue 8 Pages 723-732
Published: August 01, 1981
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.39.723

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This article is concerned with the syntheses of polyamides and their analogs by the ring-opening polyaddition reactions of diamines with bifunctional heterocyclic compounds containing acyl groups, as an extension of the nucleophilic acyl substitution of activated carboxylic acid derivatives to polymer syntheses. After a brief introduction of the reactivity of heterocyclic compounds, aminolysis and ring-opening polyaddition reactions of five-membered lactones, five-membered cyclic imide derivatives, and four-membered heterocyclic compounds are presented. New types of polymerizations through ring-opening addition are also described.

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Novel Addition Reaction to the exo-Methylene Double Bond of Diketene

Tetsuzo KATO, Takuo CHIBA

1981Volume 39Issue 8 Pages 733-740
Published: August 01, 1981
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.39.733

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This paper describes addition reaction of exo-methylene double bond of diketene to give the product keeping the β-lactone ring intact. Emphasis is placed on the reaction with double bond compounds such as olefin, carbonyl, and azo compounds to give the spiro-oxetanones.

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Recent Advances of the Preparation of Thiocyanates

Shinya HARUSAWA, Takayuki SHIOIRI

1981Volume 39Issue 8 Pages 741-753
Published: August 01, 1981
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.39.741

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Recent advances of the preparation of thiocyanates are reviewed, in which the following items are covered. 1) Preparation of thiocyanates by reaction of isothiocyanic acid or its salts with organic compounds. 2) Preparation of thiocyanates by reaction of thiocyanogen or related reagents with organic compounds. 3) Preparation of thiocyanates by modification of organo-sulfur compounds. 4) Preparation of thiocyanates by miscellaneous methods.

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Report on the 5th Winter Conference on Fluorine Chemistry

Takeshi NAKAI

1981Volume 39Issue 8 Pages 754-758
Published: August 01, 1981
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.39.754

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The 5th Winter Fluorine Conference was held at Daytona Beach, Florida, on February 1-6, 1981, under the sponsorship of Division of Fluorine Chemistry, American Chemical Society. This article not only surveys organic chemistry papers presented at the Conference but also describes how the author attending the Conference felt and what he was impressed with.

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Erratum

1981Volume 39Issue 8 Pages 773-774
Published: 1981
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.39.8_773

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