Nitrosocarbonyl Hetero-Diels–Alder Cycloaddition:
A New Tool for Conjugation
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Abstract
It
is demonstrated that nitrosocarbonyl hetero-Diels–Alder
chemistry is an efficient and versatile reaction that can be applied
in macromolecular synthesis. Polyethylene glycol functionalized with
a hydroxamic acid moiety undergoes facile coupling with 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.
The resulting block copolymers were analyzed and characterized using
GPC and NMR. The product materials could be subjected to thermal retro
[4 + 2] cycloaddition, allowing for the liberation of the individual
polymer chains and subsequent recycling of the diene-terminated polymers