The
synthesis of four different monofunctional vinyl cyclopropane
(VCP) derivatives and their polymerization behavior is presented.
The different VCPs have different capabilities to form hydrogen bonds
in their side chain. A preorganization due to these hydrogen bonds
should lead to a fast polymerization. Kinetic studies, hydrogen-bond
strength, and theoretical calculations were used to correlate the
degree of conversion and the amount of preorganization. While VCPs
capable of hydrogen bonding did not show a huge difference, a general
effect of hydrogen bonds on polymerization behavior could be observed.