Synthesis and polymerization of an alkene-substituted norbornylene

✍ Scribed by Dekking, Henri G. G.

• Publisher: John Wiley and Sons
• Year: 1961
• Weight: 277 KB
• Volume: 55
• Category: Article
• ISSN: 0022-3832
• DOI: 10.1002/pol.1961.1205516211

✦ Synopsis

Abstract

Bicyclo[2.2.1]‐hept‐2‐ene‐5‐butylene was synthesized in 20% yield by reacting equimolar amounts of cyclopentadiene and 1,5‐hexadiene at 190°C. for 16 hr. The same product was obtained by forming the Diels‐Alder adduct of cyclopentadiene and allylchloride (60% yield), making this adduct react with magnesium to form the Grignard reagent (99% yield), and then coupling the Grignard reagent with allylbromide (46% yield). The monomer was polymerized at 25°C. by means of a LiAl(decyl)~4~‐TiCl catalyst. Infrared analysis of the polymer indicates that the monomer polymerizes as a substituted norbornylene and as a cycloalkane‐substituted alpha‐olefin. The polymer is soluble in benzene and softens at 150°C.