Photochemical transformation of β,β′-dithienyl substituted o-divinylbenzenes leading to 1,2-dihydronaphthalenes or fused pentacyclic compounds: first evidence of electrocyclization process via 2,3-dihydronaphthalene intermediates

被引：18

作者：

Vuk, Dragana ^{[1
]}

Marinic, Zeljko ^{[2
]}

Molcanov, Kresimir ^{[3
]}

Kojic-Prodic, Biserka ^{[3
]}

Sindler-Kulyk, Marija ^{[1
]}

机构：

[1] Univ Zagreb, Dept Organ Chem, Fac Chem Engn & Technol, Zagreb 10000, Croatia

[2] Rudjer Boskovic Inst, Ctr NMR, Zagreb 10000, Croatia

[3] Rudjer Boskovic Inst, Dept Phys Chem, Zagreb 10000, Croatia

来源：

TETRAHEDRON | 2012年 / 68卷 / 34期

关键词：

Electrocyclization; Photochemistry; Thiophenes; o-Divinylbenzenes; 1,2-DISTYRYLBENZENE; PHOTOISOMERIZATION; PHOTOBEHAVIOR;

D O I：

10.1016/j.tet.2012.06.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photochemical behaviour of 2,2'-(o-phenylenedivinylene)dithiophenes (7a-c), 3,3'-(o-phenylenedivinylene)dithiophene (8a) and 3,3'-(o-phenylenedivinylene)dibenzothiophene (8b) was studied under the low concentrations. An intramolecular reaction via the 2,3-dihydronaphthalene intermediate has been observed in all studied examples accompanied by dimerization and polymerization. The 1,2-dihydro-2,3-dithienylnaphthalenes (9a-c) were isolated (7-9%) from the 2-thiophene derivatives while the 3-thiophene derivatives gave polycyclic structures (13-44% yield). (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6873 / 6880

页数：8