We have developed an efficient synthetic platform for the preparation of a new class of high performance thermosets based on the 1,3-dipolar cycloaddition of a bifunctional sydnone with a trifunctional alkyne. These processable materials possess outstanding thermal stability, with Td5% of 520 °C and a weight loss of <0.1% per day at 225 °C (both in air). Key to this performance is the stability of the starting functional groups that allows for reactive B-staging via simple thermal activation to give fully aromatic and highly cross-linked polypyrazole-based thermosets.

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Treatment of 5-iodo-1-(methylthio)-1-(p-tolylsulfonyl)-1-pentene with (n-Bu)3SnH and AIBN gave [(methylthio)(p-tolylsulfonyl)methyl]cyclobutane. This is due to the stability of an intermediary radical attached to methylthio and p-tolylsulfonyl groups.

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