Ring-opening metathesis polymerization (ROMP) is a powerful method for the preparation of polymers with controlled structure and functionality. In the case of cyclooctene, many substituted variants have been prepared and subjected to ROMP conditions to give the corresponding funcationalized polyalkenamers with substituents placed along the backbone every eighth carbon on average. In nearly all the examples reported to date, relatively low degrees of stereo- and regioselectivity have been observed. We recently discovered that ROMP of 3-substitued cyclooctenes gives rise to polymer structures that exhibit very high degrees uniformity with respect to the geometry of the olefin in the backbone and the placement of substituent along the backbone. For example, the ROMP 3-phenyl cyclooctene using a ruthenium-based metathesis catalyst gives greater than 98% trans double bonds and greater than 99% head-to-tail regiochemistry. In this presentation, the utility of the ROMP of 3-substituted cyclooctenes for the preparation of such sequence specific co-, ter-, and block polymers will be presented. One ultimate goal of the work is to prepare sequence specific quarterpolymers by the ROMP of tetrasubstituted cyclooctenes as shown below.

Sequence specific co-, ter-, and block polymers by ROMP

246th National Meeting (2013)

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