Journal of Synthetic Organic Chemistry, Japan

Photoreactions in Synthetic Organic Chemistry

Published: February 03, 2025 Updated: February 03, 2025

Displaying 1-20 of 26 articles

Volume 24 (1966) Issue 1 Pages 2-15 Published: February 03, 2025
Recent Advances in Organic Photochemistry
Yoshio OOTUJI

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Volume 26 (1968) Issue 5 Pages 412-423 Published: February 03, 2025
Recent Progress in Organic Photochemistry
Ikuzo TANAKA, Haruo SHIZUKA

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Volume 27 (1969) Issue 6 Pages 507-523 Published: February 03, 2025
Charge Transfer Phenomena and Photochemical Reactions
Shigeo TAZUKE

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Volume 27 (1969) Issue 12 Pages 1131-1152 Published: February 03, 2025
Mechanisms of Organic Photochemical Reactions
Teruo MATSUURA, Katsuyuki OGURA

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Volume 30 (1972) Issue 8 Pages 694-708 Published: February 03, 2025
Chemistry of Quadricyclane
Iwao TABUSHI, Kazuo YAMAMURA

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Volume 30 (1972) Issue 12 Pages 1006-1018 Published: February 03, 2025
Photochemistry of Carbon-Nitrogen Double Bonds
Hiroyuki OHTA, Katsumi TOKUMARU

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Volume 32 (1974) Issue 5 Pages 348-361 Published: February 03, 2025
Photochemistry of Anthraquinone Derivatives
Haruo INOUE, Mitsuhiko HIDA

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Volume 32 (1974) Issue 5 Pages 375-382 Published: February 03, 2025
On the Possible Role of Photochemistry, Today and Tomorrow
Katsumi TOKUMARU

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Volume 36 (1978) Issue 12 Pages 1009-1022 Published: February 03, 2025
Photochemistry of Nucleic Acid Bases
Isao SMTO, Satoru ITO

Photochemical reactions of pyrimidine and purine bases are reviewed. These include photodimerization, photohydration, and photoadditions of pyrimidine bases. Photoadditions of nucleic acid with a wide variety of compounds are also described. In particular, photoinduced addition of amino acids to nucleic acid constituents are discussed in connection with the photoinduced cross-linking of nucleic acids to proteins.
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Volume 38 (1980) Issue 4 Pages 351-360 Published: February 03, 2025
Syntheses of Medium- and Macro-Cyclic Compounds by Photochemical Reactions
Kazuhiro MARUYAMA, Yasuo KUBO

Photochemical reactions related on the synthesis of medium- and macrocyclic compounds are reviewed. This article is constructed by the following chapters : (i) photochemistry of p-benzophenone carboxylic esters, (ii) photo-cycloaddition of intramolecular two identical chromophores, (iii) photo-cyclization of intramolecular electron donor-acceptor pairs, (iv) α-cleavage reaction of carbonyl compounds, (v) electrocyclic reactions, and (vi) others.
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Volume 39 (1981) Issue 8 Pages 701-711 Published: February 03, 2025
Prediction of Directional Selectivity of Photoreactions by Molecular Orbital Theory
Takahiro TEZUKA, Osamu KIKUCHI, K. N. HOUK

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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Volume 40 (1982) Issue 11 Pages 979-985 Published: February 03, 2025
Current Trends in Organic Photochemistry
Teruo MATSUURA

The recent developments of organic photochemistry in organic synthesis, chemical conversion of solar energy, approaches to photobiological problems, applications to information technology and others, are briefly surveyed.
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Volume 44 (1986) Issue 11 Pages 1058-1070 Published: February 03, 2025
Synthesis of Biologically Active Compounds Using Photochemical Pericyclic Reactions
Chikara KANEKO, Masayuki SATO, Nobuya KATAGIRI

Novel 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.
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Volume 44 (1986) Issue 11 Pages 1029-1046 Published: February 03, 2025
Organic Synthesis based on Photoinduced Reactions
Hiroshi SUGINOME

Photoinduced 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.
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Volume 46 (1988) Issue 8 Pages 767-775 Published: February 03, 2025
[2+2] Topochemical Photoreaction
Masaki HASEGAWA

[2 + 2] Topochemical photoreaction is reviewed focussing on the photopolymerization of diolefin crystals.
In α-type crystal of olefin compounds, double bonds make contact at a distance of approximately 4 Å across a center of symmetry and, on photoirradiation it gives a centrosymmetric cyclobutane dimer (1-dimer). A β-type crystal is characterized by a lattice with one axial length of 4Å between translationally related molecules, and gives a dimer of mirror symmetry (m-dimer). In a typical topochemical photoreaction of these olefin compounds, the reaction proceeds stereospecifically with the retention of space group of the starting crystal.
In the polymerization of α-type diolefin crystals, highly crystalline linear high polymers are obtained in extremely high yields. On the other hand, from the β-type diolefin crystals, crystalline or amorphous oligomers having a zigzag main chain, or cyclophanes are obtained. Topochemical studies of unsymmetric diolefin crystals have revealed a great variety of reaction behaviors and of photoproduct configurations which are influenced strictly by a slight modification of chemical structures. The polymers having new types of alternating chain structures are prepared from unsymmetric diolefin crystals. These polymers are expected to be promising functional materials. The optically active oligomeric substances are prepared from the prochiral unsymmetric diolefin compounds through the topochemical photoreaction of chiral crystal. Lattice energy calculation has been recently applied to explain the structure-reactivity correlation including the exceptional behavior of [2+2] topochemical photoreations.
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Volume 47 (1989) Issue 11 Pages 1006-1016 Published: February 03, 2025
[2+2] Photocyclization and Photoreversion in Polymer Chemistry
Kazuhiko SAIGO

[2 + 2] Photocyclization and photoreversion in polymer chemistry is briefly described as well as the properties and functions of the resulting polymers. [2 + 2] Photocyclization is successfully applied in 1) crosslinking between the side chains and between the main chains of polymers in solid state, 2) polymerization of conjugated diolefins in crystalline state, and 3) solution polymerization of bisolefins These reactions afford the formation of image. Polymers having cyclobutanes in main chain can be also prepared by the use of the photocyclodimers of olefins. Among them, anti head-to-head coumarin dimer is susceptible to nucleophilic attack to give high-molecular-weight polyamides by the reaction with diamines. Some of the polyamides show an unique photochemical behavior and have chiral recognition ability
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Volume 48 (1990) Issue 6 Pages 536-547 Published: February 03, 2025
Laser-Induced Organic Synthesis.
Tetsuro MAJIMA

Recent studies of laser-induced organic synthesis (LIOS) are reviewed. This review describes :
1. introduction of LIOS,
2. characteristics of LIOS,
3. economics of LIOS,
4. LIOS by UV and visible lasers;
(a) medicine and related compounds,
(b) chemical products by radical chain-reactions,
(c) laser-induced catalytic reactions,
(d) addition reactions,
(e) asymmetric syntheses by circular polarized lasers,
5. LIOS by UV and visible lasers involving multiple-photon processes ;
(a) reactions in highly excited electronic states,
(b) reactions through multiphoton ionization,
(c) reactions of photochemical intermediates with high concentrations,
(d) reactions via laser ablation,
6. LIOS by a CO₂ laser,
7. development of LIOS in the future.
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Volume 50 (1992) Issue 9 Pages 798-807 Published: February 03, 2025
Photochemical Reactions of Triarylmethane Derivatives
Yoshiki OKAMOTO, Min SHI, Setsuo TAKAMUKU

Dimethyl triarylmethylphosphonates, 1, 1, 1-triary1-2-alkynes, and triarylmethylcycloalkanes underwent photochemical α, α-elimination of two aryl groups to give biaryl and the corresponding arylcarbene intermediates, respectively. Moreover, 1, 1, 1-tripheny1-2-alkene or methyl triphenylacetate also underwent another type of α, α-elimination of a phenyl group and an alkenyl group or a methoxycarbonyl group to give phenylakene or methyl benzoate, and diphenylcarbene intermediates, respctively. Triarylacetonitrile and (triphenylmethyl) diethylamine mainly underwent C-CN or C-N bond cleavage to give triarylmethane or triarylmethyl methyl ether in methanol solution. These photochemical α, α-eliminations can be understood in terms of a special example of di-π-methane or oxa-di-π-methane rearrangement through a singlet excited state.
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Volume 53 (1995) Issue 5 Pages 348-357 Published: February 03, 2025
Asymmetric Synthesis Through Photosensitization : State of the Art
Yoshihisa INOUE

Recent advances in photochemical asymmetric syntheses through photosensitization with optically active compounds have been reviewed. In sharp contrast to the flourishing studies on thermal asymmetric synthesis, asymmetric photochmistry does not appear to have attracted much attention of synthetic organic chemists until very recently, except for the diastereodifferentiating photochemical reactions of optically active substrates' carrying chiral handles. This is simply because the other modes of asymmetric photochemistry do not provide satisfactory optical yields applicable to synthetic reactions However, recent efforts in the study of photosensitized asymmetric reactions via intimately interacting exciplexes not only materialized photochemical chirality multiplication with optical yields exceeding 90%, but also revealed that the product's chirality is totally inverted by changing the reaction temperature and consequently the optical yield increases with raising temperature beyond the equipodal temperature (T₀). This unusual chirality switching by temperature has been attributed to the vital contribution of the entropy factor in the enantiodifferentiation process, which originates most probably from dynamic, synchronized conformational changes in the exciplex intermediate involving both sensitizer and substrate molecules. The present status and future perspective of photosensitized enantiodifferentiating geometrical isomerization, deracemization, [2+2] and [4+2] cycloadditions, and polar addition are discussed. Also presented are some tentative guidelines for getting higher optical yields in uni- and bimolecular asymmetric photosensitizations.
This paper is dedicated to Prof. Dr. Hans-Dieter Scharf on the occasion of his 65th birthday.
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Volume 54 (1996) Issue 7 Pages 596-606 Published: February 03, 2025
Molecular Processes in Bioluminescence of the Jellyfish Aequorea victoria
Takashi HIRANO, Mamoru OHASHI

The photoprotein aequorin isolated from the jellyfish Aequorea victoria emits blue light in the presence of Ca²⁺ with a high quantum yield. Aequorin consists of apoaequorin (apoprotein), coelenterazine, and molecular oxygen. Coelenterazine also has a chemiluminescent reactivity with oxygen. In vivo, the excited energy generated by aequorin is transferred to a green fluorescent protein (GFP), which emits green light after energy transfer. The molecular processes in the jellyfish bioluminescence have been studied for designing a highly efficient luminescent compound and for establishing the supramolecular interaction between coelenterazine and apoaequorin as well as the interaction between aequorin and GFP. This review describes the chemiluminescent reaction mechanism of coelenterazine, the supramolecular structure and the bioluminescent character of aequorin investigated by the use of chemically modified coelenterazines and apoaequorin mutants, and the character of GFP.
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