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Volume 44, Issue 11
Displaying 1-13 of 13 articles from this issue
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[in Japanese]1986 Volume 44 Issue 11 Pages 973
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSDownload PDF (209K) -
Wataru ANDO, Takeshi AKASAKA, Toshikazu TAKATA1986 Volume 44 Issue 11 Pages 974-985
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThis article reviews the current research interest in the selective preparation of hydroperoxides in photosensitized oxygenation.This involves two sections; (i) selective formation of allylic hydroperoxides by ene type reaction of olefins with singlet oxygen and (ii) stereospecific preparation of α-hydroperoxysulfide with singlet oxygen oxidation of thiazolidine derivatives.View full abstractDownload PDF (1246K) -
Tsutomu MIYASHI, Masaki KAMATA1986 Volume 44 Issue 11 Pages 986-998
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThis review describes the recent studies on organic photoreactions via charge-transfer complexes of small-ring compounds with various electron-acceptors, such as valence isomerizations, rearrangements, cycloadditions and oxygenations. In especial, mechanisms of oxygenations of three-membered compounds through the charge-transfer complexes with TCNE were discussed in detail, comparing with those reported for photoelectron transfer induced oxygenations.View full abstractDownload PDF (1554K) -
Tatsuo ARAI, Katsumi TOKUMARU1986 Volume 44 Issue 11 Pages 999-1009
Published: November 01, 1986
Released on J-STAGE: January 22, 2010
JOURNAL FREE ACCESSContrary to the hitherto accepted concept that every olefins undergo mutual isomerization between their cis-and trans-isomers, olefins substituted by anthracenyl and other aromatic polycyclic groups undergo only one-way isomerization from their cis-to trans-isomers, and the reverse isomerization from their trans-tocis-isomers never occurs. The mechanism for the one-way isomerization and the features to distinguish one-way or two-way isomerization is discussed to get whole view of the isomerization of olefins.View full abstractDownload PDF (1198K) -
Kazuhiko MIZUNO1986 Volume 44 Issue 11 Pages 1010-1021
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThe reactivity features of the following photoreactions which proceed via exciplexes or radical ion species are described: (1) Regio-and stereoselective photocycloadditions between electron-donative and electron-attractive compounds via exciplexes. (2) inter- and intramolecular photocycloaddition of vinyl ethers through termolecular interactions. (3) Photocross- addition between two different electron- rich compounds via photoinduced electron transfer. (4) Photochemistry of 9, 10- dicyanoanthracene (DCA)- 1, 2- diarylcyclopropane system; (4π + 2 σ) photocycloaddition and cis-trans photoisomerization of cyclopropane derivatives via radical cation species. (5) DCA- sensitized photooxygenation of cyclopropane derivatives and polycyclic aromatics via photoinduced electron transfer. (6) DCA- Cu (II) sensitized two-electron oxidation of cyclopropane derivatives and alkenes. (7) Photoallylation of dicyanoaromatics and α, β-unsaturated nitriles by allylic silanes. (8) Double vicinal C-C bond formation of benzylidene malononitriles by use of allylic stannanes and alkyl iodides.View full abstractDownload PDF (1235K) -
Development of Potentially Useful Reactions for Molecular BiologyIsao SAITO1986 Volume 44 Issue 11 Pages 1022-1028
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThe author's results on the organic photochemistry of nucleic acid derivatives have been reviewed. These include, i) a novel photoreaction between thymidine and primary amines, ii) its use in determining T residues of DNA fragments in DNA sequencing, iii) new photochemical methods for C-C bond formation at C- 5 and C- 6 positions of pyrimidine nucleosides, and iv) a selective deoxygenation method of ribonucleosides to 2'- deoxy-and 2', 3'-dideoxyribonucleosides by utilizing photosensitized electoron-transfer reaction.View full abstractDownload PDF (783K) -
Hiroshi SUGINOME1986 Volume 44 Issue 11 Pages 1029-1046
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSPhotoinduced reactions have enormous potential for application in organic synthesis. The present review illustrates some of the recently published significant syntheses of complex natural or unnatural molecules using the photoreactions of carbonyl compounds (Norrish type I and type II reactions and oxetan formation) and enone photocycloadditions as their key step. Some of the newly developed synthetic methods which use photoreactions of carbonyl compounds and enone photocycloadditions are also discussed.View full abstractDownload PDF (1474K) -
Shuji ICHIKAWA, Tadashi SATO1986 Volume 44 Issue 11 Pages 1047-1057
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSThe metal-catalyzed photoreaction was carried out on some sugar molecules. Under the irradiation in the presence of titanium (IV) chloride in methanol, D- glucose, D- mannose, or D- galactose underwent a selective bond cleavage at the C5-C6 position, producing the corresponding pentodialdose derivatives, while these aldohexoses underwent the selective bond cleavage at the C1-C2 position under the irradiation in the presence of iron (III) chloride in pyridine, producing aldopentoses. Both reactions are considered to proceed through an electron transfer within a metal chelate. Synthetic utilities of the products were discussed.View full abstractDownload PDF (1295K) -
Chikara KANEKO, Masayuki SATO, Nobuya KATAGIRI1986 Volume 44 Issue 11 Pages 1058-1070
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSNovel Synthetic approaches to β-lactams and Corey lactone analogues via four-membered ring intermediates formed by photochemical pericyclic reaction, followed by subsequent retro-aldol-type C-C bond fission are described. The same approach to carbocyclic C-nucleosides which involves thermal 4 + 2 addition reaction in the first step is also reported. These examples demonstrate that pericyclic reactions, if combined with C-C bond fission of the carbocyclic rings thus formed, provide productive synthetic methods of biologically active substances which allow strict regio-and stereochemical control of the required functionality of the target molecules.View full abstractDownload PDF (1323K) -
Application to Syntheses of Nitrogen-HeterocyclesMinoru MACHIDA, Kazuaki ODA, Eisuke SATO, Yuichi KANAOKA1986 Volume 44 Issue 11 Pages 1071-1080
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSA new combination of functional groups leads to a new reactive system with excited pathways. Photoreactions of chromophoric systems consisting of a nitrogen and one or two thiocarbonyls are systematically studied, and general photochemical behavior of cyclic thioimides and aza-aromatic thiones is reviewed and discussed.View full abstractDownload PDF (1121K) -
Hitoshi TAKESHITA, Nobuo KATO1986 Volume 44 Issue 11 Pages 1081-1094
Published: November 01, 1986
Released on J-STAGE: January 22, 2010
JOURNAL FREE ACCESSPhotocycloaddition reactions as synthetic methods for carbon frameworks of terpenoids were reviewed with particular emphasis of the enolized β - diketone photocycloaddition, de Mayo reaction, of methyl 2, 4- dioxoalkanoates developed in the authors' laboratory. In contrast to simple β- diketone, e.g., acetylacetone, methyl-2, 4-dioxoalkanoates, thoroughly existing in linearly conjugated structure in various media, cycloadd regiospecifically to various olefinic compounds upon UV irradiation. Thus, conjugated olefins having other functional groups in a vicinity smoothly produced [2 + 2] π cycloadducts from which further transformations could be conveniently carried out. In addition to the well- documented cyclization to cyclohexenones, the cyclopentene formation via reductive cyclization extended the usefulness of the method. Using this procedure, we have synthesized several terpenoids, from a monoterpenoid, dehydroiridodial, to a diterpene, cycloaraneosene, some of which have been discussed in detail. Although a few side reactions are found in this photocycloaddition, generality of this new version of de Mayo reaction is satisfactory.View full abstractDownload PDF (1457K) -
Sadao MIKI1986 Volume 44 Issue 11 Pages 1095-1104
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSIn the context of the importance of photoregulation of functions of organic substances, recent developement of photochromic molecules is described, focusing attention on the following topics.
a) New photochromic compounds appearring in recent literatures. b) Molecular and environment design for getting the kinetic stability of photochrome isomers. c) What kind of property of materials, into which a photochromic molecule is incorporated, can be regulated by the photoisomerization of the chromophore ? d) Hitherto unknown phenomenon accompanying photochromism.
Successful example for b) is heteroaromatic homologues of fulgide system which reveales a remarkable kinetic stability of the colored form and is immune to fatigue. A variety of properties of polymers, which are photochemically regulated, are related closely to the fundamental character of the photochromism of chromophoric unit in the polymer. Photo-voltaic phenomenon of the thin film of triphenylformazan is a unique two photon process consisting of photoisomerization of the red-form to the yellow-form and the successive photo-ionization of the latter.View full abstractDownload PDF (1229K) -
[in Japanese], [in Japanese], [in Japanese], [in Japanese], [in Japane ...1986 Volume 44 Issue 11 Pages 1105-1106
Published: November 01, 1986
Released on J-STAGE: November 13, 2009
JOURNAL FREE ACCESSDownload PDF (286K)
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