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
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