Summary: Degradation studies of cis‐1,4‐polyisoprene were carried out using first and second generation Grubbs catalysts to achieve end‐functionalized acetoxy oligomers in both an organic solvent and a latex phase at room temperature. Well‐defined acetoxy telechelic polyisoprene structures were obtained in a selective manner with a range of $\overline M _{\rm n}$ from 10 000 to 30 000, with a polydispersity index of around 2.5.
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