Intramolecular 10,10a-[2+2] photocycloaddition reactions of phenanthrenes with linked styrene

被引：7
|
作者：
Maeda, Hajime [1 ]
Nakashima, Ryota [1 ]
Sugimoto, Akira [1 ,2 ]
Mizuno, Kazuhiko [1 ]
机构：
[1] Osaka Prefecture Univ, Grad Sch Engn, Dept Appl Chem, Naka Ku, 1-1 Gakuen Cho, Sakai, Osaka 5998531, Japan
[2] Osaka Univ, Inst Sci & Ind Res SANKEN, Mihogaoka 8-1, Osaka 5670047, Japan
来源：
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY | 2016年 / 329卷
关键词：
Photocycloaddition; Phenanthrene; Styrene; Exciplex; Eight membered ring product; PHOTOCHEMICAL-REACTIONS; AROMATIC-COMPOUNDS; DIMETHYL FUMARATE; METHOXYPHENYLALKENYL PHENANTHRENECARBOXYLATES; STEREOSPECIFIC PHOTOCYCLOADDITION; 2-PI+2-PI PHOTOCYCLOADDITION; PHOTOPHYSICAL BEHAVIOR; BETA-METHYLSTYRENES; 2+2 CYCLOADDITION; SINGLET EXCIPLEX;
D O I：
10.1016/j.jphotochem.2016.07.001
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Intramolecular photocycloaddition reactions of styrene linked 9-cyanophenanthrenes led to formation of C-9 C-10 [2+2] cycloadducts which underwent cycloreversion under the prolonged irradiation conditions to regenerate the starting substrates. Unusual 8-membered ring products were irreversibly formed in these processes. Product distributions' were governed by substituent controlled, donor-acceptor interactions that direct generation of two intramolecular singlet exciplexes, which serve as intermediates in the pathways to formation of 9,10- and 10,10-[2+2] adducts. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码：232 / 237
页数：6
相关论文
共 50 条
  • [1] INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION .7. EFFICIENT INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION OF STYRENE DERIVATIVES TOWARD NEW CROWN ETHERS
    INOKUMA, S
    YAMAMOTO, T
    NISHIMURA, J
    TETRAHEDRON LETTERS, 1990, 31 (01) : 97 - 100
  • [2] Enantioselective intramolecular [2+2]-photocycloaddition reactions in solution
    Bach, Thorsten
    Bergmann, Hermann
    Harms, Klaus
    Angewandte Chemie (International Edition in English), 2000, 39 (13): : 2302 - 2304
  • [3] Enantioselective intramolecular [2+2]-photocycloaddition reactions in solution
    Bach, T
    Bergmann, H
    Harms, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (13) : 2302 - 2304
  • [4] Effects of oligooxyethylene linkage on intramolecular [2+2] photocycloaddition of styrene derivatives
    Nakamura, Y
    Fujii, T
    Inokuma, S
    Nishimura, J
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1998, 11 (02) : 79 - 83
  • [5] Conformationally restricted pyrrolidines by intramolecular [2+2] photocycloaddition reactions
    Fort, Diego A.
    Woltering, Thomas J.
    Nettekoven, Matthias
    Knust, Henner
    Bach, Thorsten
    CHEMICAL COMMUNICATIONS, 2013, 49 (29) : 2989 - 2991
  • [6] A Chiral Thiourea as a Template for Enantioselective Intramolecular [2+2] Photocycloaddition Reactions
    Mayr, Florian
    Brimioulle, Richard
    Bach, Thorsten
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16): : 6965 - 6971
  • [7] Synthesis of Fluorinated Tricyclic Scaffolds by Intramolecular [2+2] Photocycloaddition Reactions
    Fort, Diego A.
    Woltering, Thomas J.
    Nettekoven, Matthias
    Knust, Henner
    Bach, Thorsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (40) : 10169 - 10172
  • [8] Synthesis of crownophanes by means of intramolecular [2+2] photocycloaddition of styrene derivatives and their complexing ability
    Inokuma, S
    Nishimura, J
    NIPPON KAGAKU KAISHI, 1999, (05) : 305 - 316
  • [9] INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION OF OXOESTERS AND OXOAMIDES
    LEBLANC, S
    PETE, JP
    PIVA, O
    TETRAHEDRON LETTERS, 1993, 34 (04) : 635 - 638
  • [10] DIRADICAL INTERMEDIATES IN INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION
    BECKER, D
    DENEKAMP, C
    HADDAD, N
    TETRAHEDRON LETTERS, 1992, 33 (06) : 827 - 830
12345