Selective ring-opening allene metathesis polymerization (ROAlMP) and ruthenium vinylidene formation from 1,2-cyclononadiene () by simple catalyst selection are discussed. Grubbs second-generation catalyst (G2) favors the formation of an alkylidene leading to the ROAlMP of (). Grubbs first-generation catalyst (G1) favors vinylidene formation and prevents the homopolymerization of () even at elevated temperatures. Isolation and characterization of poly() by NMR analysis and MALDI-TOF confirms the generation of a well-defined polyallene that exhibits good thermal stability ( ca. 390 °C) and fluorescent properties. Ring-opening metathesis polymerization (ROMP) of a highly strained norbornene derivative (NBE-Pr) at 80 °C using the ruthenium vinylidene generated from () is also investigated. The discovery of ROAlMP allows for the simple access of well-defined polyallenes from commercially available catalysts and will ultimately guide structure-property determinations of polyallenes.
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