G. Butler, M. L. Miles
1966
Citations
0
Influential Citations
3
Citations
Journal
Polymer Engineering and Science
Abstract
2-Ally-1-methylenecyclohexane is a compound which is functionally capable of undergoing polymerization by the alternating intra-intermolecular propagation mechanism to produce poly[1,8-methylene[4.3.0] bicyclononane]. This monomer was synthesized and its polymerization through use of cationic and Ziegler-type initiators was studied. Synthesis of the monomer was accomplished by the following reaction sequence: (1) conversion of cyclohexanone to 2-allycyelohexanone by reaction wtih allyl bromide and sodium amide and (2) conversion of 2-allycyclohexanone to the desired monomer by reaction with the phosphorane derived from methyltriphenylphosphonium bromide. Polymerizaton was accomplished by use of boron trifluoride resulting in 44% conversion to polymer, of which 94% was soluble. Through use of infrared and nuclear magnetic resonance techniques, the soluble portion of the polymer was shown to contain 54% of bicyclic units and the remainder to be non-cyelized monomer units in which the residual unsaturation was composed predominantly of allyl groups.