Theoretical and Experimental Study of Monofunctional Vinyl Cyclopropanes Bearing Hydrogen Bond Enabling Side Chains
Sören Schumacher, Sanwardhini Pantawane, Stephan Gekle, and Seema Agarwal
Macromolecules 2021, https://doi.org/10.1021/acs.macromol.0c02490
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.