Meek, S.J., O’Brien, R.V., Llaveria, J., Schrock, R.R. and Hoveyda, A.H. (2011) Catalytic Z-selective olefin cross metathesis for natural product synthesis. Nature, 471, 461-466. doi:10.1038/nature09957

has been cited by the following article:

• TITLE: Citrus oils as chain transfer agents in the cross-metathesis degradation of polybutadiene in block copolymers using Ru-alkylidene catalysts

  AUTHORS: Araceli Martínez, Selena Gutiérrez, Mikhail A. Tlenkopatchev

  KEYWORDS: Metathesis Degradation; Polybutadiene in Block; Natural Oils; d-Limonene; Ru-Alkylidene Catalysts

  JOURNAL NAME: Natural Science, Vol.5 No.7, July 9, 2013

  ABSTRACT: The cross-metathesis degradation of poly(styrene-co-butadiene) (styrene, 30 wt%) (SB-1) and poly(styrene-co-butadiene) (styrene, 21 wt%) (SB- 2) in the presence of essential oils and d-limo-nene as chain transfer agents (CTAs) using Rualkylidene catalysts (PCy3)2(Cl)2Ru = CHPh (I) and (1,3-diphenyl-4,5-dihydroimidazol-2-ylidene) (PCy3)Cl2Ru=CHPh (II) was studied. Terpene-terminated butadiene oligomers and polystyrene blocks were obtained as products of the degradation of SB-1 and SB-2. Catalysts I and II showed high activity in the degradation of SB copolymers to produce the low molecular weight products (Mn = 276 - 335 g·mol-1) and yields ranging from 91% - 95%. The cross-metathesis degradation of copolymers in organic solvents and in citrus oils (mandarin, orange and lemon oils) proceeded with similar efficiency and resulted in the same molecular weight butadiene oligomers. According to GS/MS (EI) analysis, the main products of the degradation of SB-1 copolymer with d-limonene were limonene-terminated oligomers of series Am (m = 1 - 4).