Photobehaviour of 2- and 3-heteroaryl substituted o-divinylbenzenes; formation of fused 2,3- and 3,2-heteroareno-benzobicyclo[3.2.1]octadienes and 3-heteroaryl benzobicyclo[2.1.1]hexenes
- 作者：Dragana Vidaković ; Irena Š ; korić ; Margareta Horvat ; Ž ; eljko Marinić ; Marija Š ; indler-Kulyk
- 关键词：Oxygen heterocycles ; Sulfur heterocycles ; Furan ; Thiophene ; Photochemistry ; Photocycloaddition ; Synthesis
- 刊名：Tetrahedron
- 出版年：2008
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：28 April 2008
- 卷：64
- 期：18
- 页码：3928-3934
- 文件大小：448 K
摘要
New β-3-thienyl (trong>8 trong>) and β-3-furyl derivatives of o-divinylbenzene (trong>9 trong>) have been synthesised and their photochemical behaviour compared with 2-thienyl (trong>7 trong>) and 2-furyl derivatives (trong>2 trong>). Whereas the β-(2-heteroaryl) substituted o-divinylbenzenes (trong>7 trong> or trong>2 trong>) give only bicyclo[3.2.1]octadiene structure (trong>14 trong> or trong>1 trong>) by 1,6-ring closure of the biradical intermediate, β-(3-heteroaryl) substituted o-divinylbenzenes (trong>8 trong> or trong>9 trong>) give bicyclo[3.2.1]octadiene structure (trong>23 trong> or trong>24 trong>) and bicyclo[2.1.1]hexene structure (trong>25 trong> or trong>26 trong>) by 1,6- and 1,4-ring closure, respectively. This photochemical approach provides a simple method to 2,3- and 3,2-fused thiophene and furan polycyclic compounds.