It is demonstrated that nitrosocarbonyl Diels�Alder chemistry can be applied in macromolecular synthesis. Polyethylene glycol functionalized with a hydroxamic acid moiety, can be coupled to cyclopentadiene terminated polystyrene, through a copper catalyzed, as well as thermal hetero Diels�Alder reaction.The mild and orthogonal methods used to carry out this reaction make it an attractive method for the synthesis of block copolymers. Using GPC and NMR, the resulting block copolymers were analyzed and characterized. The product materials were subjected to thermal retro [4+2] cycloaddition, allowing for the liberation of the individual polymer chains, and subsequent recycling of the diene terminated polymers.

Nitrosocarbonyl hetero-Diels�Alder cycloaddition: A versatile new tool for conjugate formation

248th National Meeting (2014)

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