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Volume 43, Issue 6
Displaying 1-17 of 17 articles from this issue
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General SurveyTatsuya SHONO1985 Volume 43 Issue 6 Pages 491-495
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThe potentiality of electroorganic chemistry in organic synthesis is briefly surveyed by exemplifying following three categories.
(1) Organic synthesis using anodic oxidation of amides or carbamates as the key step.
(2) Reactions using mediators.
(3) Generation of bases under the conditions of electroreduction, and their utilization in organic synthesis.
The potentiality of commercialization of electroorganic methods is also briefly discussed.View full abstractDownload PDF (594K) -
Yoshihiro MATSUMURA1985 Volume 43 Issue 6 Pages 496-510
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThis article surveys electroreductions of organic compounds from a viewpoint of organic synthesis. The reactions are classified into the following categories.
(1) Simple reduction ; (1) -1 Reduction of aromatic nucleus, carbon-carbon double and triple bonds, (1) -2 Reduction of C= X (X=O, N), (1) -3 Reduction of carboxylic acid, ester, amide, imide, and nitrile, (1) -4 Reduction of C-X (X=halogen, O, N), (1) -5 Reduction of X-Y, (1) -6 Reduction of nitro group.
(2) Dimerization.
(3) Reaction of cathodically generated active species with electrophile ; (3) -1 Alkylation, (3) -2 Acylation, (3) -3 Carboxylation, (3) -4 Anionic chain reaction.
(4) Elimination ; (4) -1 1, 1-Elimination, (4) -2 1, 2-Elimination, (4) -3 1, 3-Elimination, (4) -4 1, n-Elimination.View full abstractDownload PDF (1489K) -
Hideo TANAKA1985 Volume 43 Issue 6 Pages 511-521
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThis review deals with the electrooxidative and electroreductive carbon-carbon bond making reactions. Various ideas approaching to the carbon-carbon bond making are discussed by making a survey of papers which have appeared in the last several years.View full abstractDownload PDF (1049K) -
Masao TOKUDA1985 Volume 43 Issue 6 Pages 522-532
Published: June 01, 1985
Released on J-STAGE: January 21, 2010
JOURNAL FREE ACCESSThe electrochemical reactions of organometallic compounds along with recent studies on their syntheses are briefly described from the standpoints of organic synthesis. This review deals with carbon-carbon bond formation by a coupling and an introduction reaction of alkyl groups of organometallics, carbon-metal bond formation, metal-metal bond formation, demetallation, synthetic reaction utilizing active organometallic species, and an effect of bonding metal in electroorganic reactions.View full abstractDownload PDF (1163K) -
Potentiality of Electro - reductive and -oxidative Functionalizations in ElectrosynthesisSigeru TORII, Tsutomu INOKUCHI1985 Volume 43 Issue 6 Pages 533-548
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThis review deals with indirect electro-reductive and oxidative reactions which involve four major topics : (1) Electroreductive functionalization with metal redox complexes as mediators ; (2) Electroreductive functionalization with organic redox compounds as mediators ; (3) Electroreductive functionalization with superoxide ; (4) Electrooxidative functionalization with miscellaneous redox systems.View full abstractDownload PDF (1684K) -
Shigenori KASHIMURA1985 Volume 43 Issue 6 Pages 549-556
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSAlthough a number of useful synthetic reactions using bases as catalysts have been studied, the types of bases available are rather limited, and hence the formation of basic species under the conditions of electroreduction has attracted much attention from mechanistic and synthetic points of view. The use of such bases generated under the conditions of electroreduction often promotes the useful synthetic reactions such as condensations, rearrangements, and the alkylation of compounds having active hydrogen atoms with high yields and selectivities. In this article, followings are described from a view point of organic synthesis.
1) The formation and the classification of these bases generated under the conditions of electroreduction.
2) The examples of useful synthetic reactions using these bases.View full abstractDownload PDF (840K) -
How to generate EGA and how to utilize itKenji UNEYAMA1985 Volume 43 Issue 6 Pages 557-564
Published: June 01, 1985
Released on J-STAGE: January 22, 2010
JOURNAL FREE ACCESSThis review summarizes : (1) electrolysis conditions useful for the effective generation of electrogenerated acid (EGA), (2) discussion on the generation mechanism of EGA, and (3) the recently developed EGA-catalyzed reactions for the selective organic functional group transformation.View full abstractDownload PDF (806K) -
Tsutomu NONAKA, Toshio FUCHIGAMI1985 Volume 43 Issue 6 Pages 565-574
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThis review is organized under the following headings with 120 references.
1. Introduction
2. Kind and Function of Modified Electrodes
2. 1 Which Parts of Electrode Systems Can Be Modified ?
2. 2 What Methods Can be Available for the Modification ?
2. 3 What Functions Can Be Given by the Modification ?
3. Electroreactions Using Modified Electrodes
3. 1 Electrocatalytic Reactions
3. 1. 1 Adsorbed Electrodes
3. 1. 2 Chemically Modified Electrodes
3. 1. 3 Polymer- Coated Electrodes
3. 2 Product-Selective Electroreactions
3. 3 Substrate-Differentiating Electroreactions
3. 4 Asymmetric Electroreactions
3. 4. 1 Electrochemical Asymmetric Synthesis
3. 4. 2 Electrochemical Optical Resolution
3. 5 Photo- Catalyzed Electroreactions
3.6 Others
4. Concluding RemarksView full abstractDownload PDF (1329K) -
Zen-ichiro TAKEHARA, Zempachi OGUMI1985 Volume 43 Issue 6 Pages 575-582
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSNew electrolysis methods for electro-organic syntheses were reviewed from the viewpoint of reduetion of difficulties in work-up and material preparation processes. The two phase electrolysis method has been applied to chlorination and cyanation of some aromatic compounds, using a phase transfer catalyst such as a quaternary ammonium salt. Addition of some Lewis acids to the system caused a favorable effect on yield. An ion exchange membrane was utilized as a supporting electrolyte using a conventional cell of two compartment equipped with a fine platinum mesh electrode pressed on the ion exchange membrane. An SPE electrolysis method was applied to electro-organic syntheses. The feasibility of the method was examined in some systems including mediatory systems fixed in an SPE material, usually Nafion. The fundamental properties of three methods were also reviewed.View full abstractDownload PDF (881K) -
Shosuke YAMAMURA1985 Volume 43 Issue 6 Pages 583-593
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSFrom a biogenetic point of view, a number of bioactive lignans and neolignans formed by the oxidative dimerization of various C6-C3 units are regio- and stereo-selectively synthesized using electrochemical method, in which anodic oxidation of the corresponding phenols as a key-step is carried out under various conditions. Particularly, a simple method leading to the formation of bicyclo [3. 2. 1] octanones is demonstrated.View full abstractDownload PDF (1018K) -
Isao KITAGAWA, Masayuki YOSHIKAWA1985 Volume 43 Issue 6 Pages 594-602
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSBy use of electrochemical reactions, aldonic acids, alditols, and aminocyclitols have been synthesized. Electrochemical reactions have also been utilized for removal of protecting groups in various syntheses and for chemical modifications of triterpene-oligosides, nucleosides, and aminoglycoside-antibiotics. This article reviews recent topics on functional group modifications and chem ical modifications and syntheses of carbohydrates and related compounds where electrochemical oxidations and reductions have been used as key-reactions.View full abstractDownload PDF (934K) -
A Facile Removal of the Arenesulfonyl Group by Electrochemical Reduction in a New Cooperative SystemSyntheses and Structural Analyses of 1- Benzazocinone DerivativesTakeshi OHNUMA, Kuniyuki ODA, Yoshio BAN1985 Volume 43 Issue 6 Pages 603-609
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThe arenesulfonyl group of sulfonamide (12) was efficiently removed by utilization of electrochemical reduction in a new cooperative system of anthracene and ascorbic acid, and subsequent electrogenerated bases were very effective to produce the 1-benzazocinone derivatives, in one pot, through the controlled crisscross annulation.View full abstractDownload PDF (760K) -
Tameo IWASAKI, Hiroshi HORIKAWA1985 Volume 43 Issue 6 Pages 610-616
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThe amino and carboxylic groups of amino acids and the side chain of several amino acids are active electrochemically and the sugar moiety of nucleosides is also active. Thus, a variety of transformations are possible by applying electrode reaction to amino acids and nucleosides. In this review is described the synthesis of a new type of amino acids and nucleosides utilizing electrode reaction which has been done mainly in the authors' laboratory for the last decade. The following items are included. (1) Transformation utilizing the amino and carboxylic groups of amino acids. (2) Transformation utilizing the side chain of amino acids. (3) Transformation of amino acids into nucleic acid pyrimidine bases. (4) Synthesis of unnatural nucleosides.View full abstractDownload PDF (837K) -
Ikuzo NISHIGUCHI1985 Volume 43 Issue 6 Pages 617-633
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThis article contains a variety of laboratory-scale experimental methods for electroorganic synthesis, which may probably give practical guidelines or some clues to a synthetic organic chemist who has not been famililar with this specific but useful technique in organic synthesis in spite of his much interest.
Following items are explained mainly in order to seek good answers for many problems, such as how to get easy availability of equipment, simplicity of procedure, solution of various experimetal trouble and optimum reaction conditions.
1) Preface
2) Equipment to prepare.
3) Various type of methods and practical examples of electroorganic synthesis.
4) Experimental factors controlling electroorganic reaction -Searching of optimum reaction conditions-
5) Final comment
As this specific reaction may be generally controlled by more experimental factors than ordinary chemical reaction in solution, more “try and error” may be required to get optimum conditions, hopefully, by simpler equipment and procedure.View full abstractDownload PDF (2392K) -
Trend in Patent ApplicationsTsuneaki HIRASHIMA, Ikuzo NISHIGUCHI1985 Volume 43 Issue 6 Pages 634-647
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSIn recent years, new industrial uses of electroorganic synthesis have been spurred by much advances in the fields of its chemistry, engineering and material. In the light of a variety of merits and demerits of this specific technique in comparison with other chemical methods, it may be applied to production of highly valuable compounds, particularly pharmaceutical drugs, pesticides, perfume and high-qualified color-stuff, more favorably than to that of commodity chemicals.
This review article deals wich specific characters of electroorganic synthesis from the viewpoint of industrial applications, presently commercialized electroorganic processes, current aspect of research and development, and some useful examples of electroorganic reactions described in recently applied patents.View full abstractDownload PDF (1714K) -
Takuo KAWAHARA1985 Volume 43 Issue 6 Pages 648-653
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSRecent studies on the organic electrosynthesis and development of new electrolysis technique around chlorine-alkali production technology using ion exchange membrane promote industrialization of organic synthesis by electrolysis. This paper describes how to expand scale of an electrolyzer, and what are important factors in designing the electrolyzer.View full abstractDownload PDF (563K) -
[in Japanese], [in Japanese], [in Japanese], [in Japanese]1985 Volume 43 Issue 6 Pages 654
Published: June 01, 1985
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSDownload PDF (165K)
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