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

1,3-Bis [(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes 1 [RO: CH3O (a), C2H5O (b)] were synthesized by the esterification of the corresp onding 1-alkoxycarbonyl-2-vinylcyclopropane-1-carboxylic acids with resorci nol. The structure of the new vinylcyclopropanes was confirmed by elemental analysis and infrared (IR), H-1 nuclear magnetic resonance (H-1-NMR), and C-13 nuclear magnetic resonance (C-13- NMR) spectroscopy. The radical polym erization of difunctional. 2-vinyl-cyclopropanes in bulk with 2,2'-azoisobu tyronitrile (AIBN) results in hard, transparent, crosslinked polymers. Duri ng the bulk polymerization of the crystalline bis [(1-methoxycarbonyl-2-vin ylcyclopropane-1-yl)carboxy]benzene la, an expansion in volume of about 1% took place. The radical solution polymerization of la resulted in a soluble polymer with pendant 2-vinylcyclopropane groups. (C) 1999 John Wiley & Son s, Inc. J Appl Polym Sci 72: 1775-1782, 1999.