Isocyanoethyl methacrylate

Hexamethyltriethylenetetraamine Isocyanoethyl methacrylate Iodine transfer polymerization Liquid chromatography Living radical polymerizations... 

The polymerizable double bond may be obtained by functionalizing the amine with a monomer such as methacrylate glycidyl ether or isocyanoethyl methacrylate (IEM), i.e., reaction of amine with an epoxy or isocyanate group. We chose to functionalize the amine by using maleic anhydride to get highly stable (thermally) maleimide macromonomers [162], as shown in Scheme 49. 

Scheme 50 Synthesis of macromonomers from isocyanoethyl methacrylate. MMA methyl methacrylate, Magly methacrylate glycidyl ether, DMAEMA 2-(dimethylamino)ethyl methacrylate...

It is important to note that the thiol-isocyanate reaction is not orthogonal to the base-catalyzed Michael addition of thiols to alkenes, as was observed by Lowe when attempting to conjugate 2-isocyanoethyl methacrylate, although this system still showed significant selectivity towards the thiocarbamate adduct (Li et al, 2009). Furthermore, it should be noted that isocyanates are very reactive (and toxic) compounds that can react with hydroxyl functionality. 

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