Preparation and ring-opening metathesis polymerizations of 5-siloxydeltacyclene and deltacyclene using the Schrock molybdenum alkylidene catalyst

The living ring-opening metathesis polymns. of deltacyclene (I) and 5-(tert-butyldimethylsiloxy)deltacyclene (II) in presence of the Schrock catalyst Mo(=CHCMe2Ph)[=N-2,6-(iso-Pr)2Ph](O-tert-Bu)2 were described. II was prepd. by first epoxidizing I, then treating this epoxide with a Lewis acid in presence of thiophenol. The rearrangement that ensued placed an alc. at C-5 position and trapped the nucleophile at C-8 position, allowing the reintroduction of the double bond by oxidn. of the sulfide followed by a thermal elimination. The polymns. of I and II were done neat or in soln. II polymer was substantially more sol. in org. solvents than I polymer.