Polymerization of cyclic monomers. VII. Synthesis and radical polymerization of 1,3-bis[(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes

✍ Scribed by Norbert Moszner; Frank Zeuner; Thomas Völkel; Urs Karl Fischer; Volker Rheinberger

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 174 KB
• Volume: 72
• Category: Article
• ISSN: 0021-8995
• DOI: 10.1002/(sici)1097-4628(19990624)72:13<1775::aid-app13>3.0.co;2-f

✦ Synopsis

1,3-Bis[(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes 1 [RO: CH 3 O (a), C 2 H 5 O (b)] were synthesized by the esterification of the corresponding 1-alkoxycarbonyl-2-vinylcyclopropane-1-carboxylic acids with resorcinol. The structure of the new vinylcyclopropanes was confirmed by elemental analysis and infrared (IR), 1 H nuclear magnetic resonance ( 1 H-NMR), and 13 C nuclear magnetic resonance ( 13 C-NMR) spectroscopy. The radical polymerization of difunctional 2-vinyl-cyclopropanes in bulk with 2,2Ј-azoisobutyronitrile (AIBN) results in hard, transparent, crosslinked polymers. During the bulk polymerization of the crystalline bis[(1-methoxycarbonyl-2vinylcyclopropane-1-yl)carboxy]benzene 1a, an expansion in volume of about 1% took place. The radical solution polymerization of 1a resulted in a soluble polymer with pendant 2-vinylcyclopropane groups.