Science of Synthesis

Riva, R.; Banfi, L.; Basso, A., Science of Synthesis: Multicomponent Reactions, (2014) 1, 407.

The combination of the Passerini reaction with acyclic diene metathesis polymerization leads to the formation of poly[1-(alkylcarbamoyl)alkyl alkanoates] ‌180‌, a new class of polyesters having an amide moiety in their side chain (‌Scheme 73‌).[‌128‌] The carboxylic acid and the aldehyde are prepared from castor oil derived ricinoleic acid, a renewable resource, and submitted to a classical Passerini reaction to give ‌179‌. Then, the polymerization, through acyclic diene metathesis in the presence of various ruthenium(II)-based catalysts, takes place providing ‌180‌. If a bifunctional isocyanide is used, such as an isocyanoacetate (R1 = CH2CO2t-Bu), the ester hydrolysis provides a carboxylic functionality to be used for a following Passerini reaction as a grafting-onto reaction to afford ‌181‌. Alternatively, bifunctional monomers (with two carboxylic or two aldehyde functionalities) are synthesized by self metathesis and then polymerized by the Passerini reaction to give differently connected polyesters ‌182‌ (‌Scheme 73‌).

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References