ortho-Azobenzenophanes: Photochemical and Thermal Reactions of [2,2][2,2′]Azobenzenophane

✍ Scribed by Tauer, Erich ;Machinek, Reinhard

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 325 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619960723

✦ Synopsis

Abstract

The cyclic azo compounds 6 and 7 were synthesized. The chemical properties of 6 were investigated. Irradiation of the trans,trans form 6~t,t~ leads to isomerization to the trans,cis form 6~t,c~ and to the cis,cis form 6~c,c~. Compounds 6~t,c~ and 6~c,c~ can be isolated. However, thermally, 6~t,c~ and 6~c,c~ react slowly back to 6~t,t~. All attempts to convert 6 by light into the tetrazetidine 10 have been unsuccessful until now. In boiling toluene 6 undergoes an interesting rearrangement, namely a ring contraction, during which an azo group is cleaved with formation of an indole ring and a primary amino group.