有機合成化学協会誌

光反応と有機合成化学：基礎・理論から応用まで

公開日: 2025/02/03 更新日: 2025/02/03

光反応は、環境・エネルギー、生命・医農薬、材料などの研究と関連する学際領域です。有機合成化学の着眼で、長期にわたって積み上げられた広範なアプローチを集約しました。どうぞお楽しみください。
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26件中1～20件の論文を表示しています

24 巻 (1966) 1 号 p. 2-15 公開日: 2025/02/03
有機光化学反応の最近の進歩
大辻吉男

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26 巻 (1968) 5 号 p. 412-423 公開日: 2025/02/03
有機光化学の最近の進歩
田中郁三, 閑春夫

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27 巻 (1969) 6 号 p. 507-523 公開日: 2025/02/03
電荷移動と光化学反応
田附重夫

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27 巻 (1969) 12 号 p. 1131-1152 公開日: 2025/02/03
有機光化学反応の機構
松浦輝男, 小倉克之

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30 巻 (1972) 8 号 p. 694-708 公開日: 2025/02/03
クァドリシクランの化学
田伏岩夫, 山村和夫

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30 巻 (1972) 12 号 p. 1006-1018 公開日: 2025/02/03
炭素-窒素二重結合系の光化学
太田裕之, 徳丸克己

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32 巻 (1974) 5 号 p. 348-361 公開日: 2025/02/03
アントラキノン誘導体の光化学
井上晴夫, 飛田満彦

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32 巻 (1974) 5 号 p. 375-382 公開日: 2025/02/03
光化学反応のもつ可能性を探る
徳丸克己

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36 巻 (1978) 12 号 p. 1009-1022 公開日: 2025/02/03
核酸塩基の光化学反応
斉藤烈, 伊藤哲

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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38 巻 (1980) 4 号 p. 351-360 公開日: 2025/02/03
光化学反応による中・大員環化合物の合成
丸山和博, 久保恭男

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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39 巻 (1981) 8 号 p. 701-711 公開日: 2025/02/03
MO理論による光反応の配向予測
手塚敬裕, 菊池修, K. N. HOUK

MO理論にもとづき光反応の方向性を定量的に予測できるならば, 有機化学者にとっても役に立っ場合が多い。本論文では静的反応性指数にもとづく光反応位置の予測法を紹介する。特に最近我々の提出した新しい反応性指数および予測モデルにっき述べることを目的とした。しかし同時に「簡単に使えるモデル」を念頭においた。シクロヘプタトリエンの光電子環化反応における置換基効果および1, 7シグマトロピーにおける反応方向の特異性をMO理論をもとに予測し, 我々の新しい極性モデルを説明した。
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40 巻 (1982) 11 号 p. 979-985 公開日: 2025/02/03
有機光化学の進歩と展望
松浦輝男

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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44 巻 (1986) 11 号 p. 1058-1070 公開日: 2025/02/03
光化学的周辺環状反応を用いる生理活性化合物の合成
金子主税, 佐藤雅之, 片桐信弥

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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44 巻 (1986) 11 号 p. 1029-1046 公開日: 2025/02/03
光反応を機軸とする有機合成
杉野目浩

この30年間に, 励起有機分子の化学は劇的ともいえる急速な進展を遂げた。その結果, 周知のように,基底状態の反応によっては達成するのがむずかしい有機分子変換に対する手段として利用できることが明らかとなった。有機化学者によって励起分子の反応が研究されはじめた当初は, 光化学反応が,著しいひずみをもった有機分子の合成などに, 特に有効であることが実証されはしたが, 有機合成の手段として応用される範囲は限られていた。しかし, 有機合成化学の発展と軌を一にして,応用の範囲は次第にひろがり, 最近では,天然物など極めて複雑な有機分子の全合成などに決定的な役割を演じている報告が目立つ。有機分子の光化学反応に関する研究報告は, 毎年おびただしい数にのぼるが,合成の手段として有効であることが一見してわかる反応は勿論のこと, 殆んどの反応が, 分子変換の手段としての潜在能力を秘めていると言っても過言ではない。本稿においては, 最近の多数の研究成果の中から, 励起カルボニル化合物, エノンとオレフィンの光付加を中心に有機合成への光化学反応の応用に関して, 特に顕著な成功をおさめた研究例のいくつかを選んで, 光化学反応が有機合成にどのように使われているかを紹介したい。紙面の関係で, 各合成の図示にあたっては,出発分子とキーステップとして用いられた光反応のみにとどめざるを得なかったので, 詳細については,引用文献を参照していただきたい。
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46 巻 (1988) 8 号 p. 767-775 公開日: 2025/02/03
[2+2] トポケミカル光反応
長谷川正木

[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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47 巻 (1989) 11 号 p. 1006-1016 公開日: 2025/02/03
光 [2+2] 付加環化・開裂と高分子
西郷和彦

[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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48 巻 (1990) 6 号 p. 536-547 公開日: 2025/02/03
レーザー有機合成
真嶋哲朗

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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50 巻 (1992) 9 号 p. 798-807 公開日: 2025/02/03
トリフェニルメタン誘導体の光反応
岡本能樹, 施敏, 高椋節夫

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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53 巻 (1995) 5 号 p. 348-357 公開日: 2025/02/03
光増感反応で不斉合成に迫る
井上佳久

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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54 巻 (1996) 7 号 p. 596-606 公開日: 2025/02/03
オワンクラゲ生物発光の分子過程
平野誉, 大橋守

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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