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We report here the ethenolysis of squalene and natural rubber utilizing (NHC)(NHCewg)RuCl2(= CRR’) and Grubbs–Hoveyda complexes. 0.01 mol% [Ru] per double bond are sufficient for extensive squalene cleavage, resulting in the formation of numerous terminal olefins, which were identified by GC/MS. The depolymerization of natural rubber requires 0.1 mol% [Ru] and leads to the formation of various oligomeric isoprenes, several of which (n = 2–6) were isolated and characterized.
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