The Synthesis of Cyclic Ether-Containing Natural and Non-natural Products by Metathesis Reactions

Lindsay, David M.

doi:10.1007/7081_2015_197

Cited by 2 publications

(1 citation statement)

References 62 publications

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“…metathesis-isomerization reactions, 32 cyclic polymers, 33 fragrances, 34,35 pharmaceuticals, [36][37][38] and natural products. 39,40 In the specific case of α-olefin metathesis, the almost thermoneutral reaction can be driven to completion by removal of the ethylene co-product. In that context, cationic Mo imido NHC alkylidenes in both molecular (Mo + ) [41][42][43][44] and silica-supported (Mo + /SiO2) 45 forms (Fig.…”

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confidence: 99%

Molecularly defined lubricant hydrocarbons from olefin metathesis

Berkson

Björgvinsdóttir

Barnes

et al. 2023

Preprint

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Hydrocarbon-based lubricants are ubiquitous in industrial applications but are typically complex mixtures of branched molecules that are challenging to characterize and to relate to their macroscopic properties. Consequently, lubricants are typically optimized empirically for specific applications by blending base oils and organic or inorganic additives. Here, we report the synthesis and characterization of molecularly defined lubricants via metathesis of branched terminal olefins followed by hydrogenation of the internal olefin products. The resulting saturated hydrocarbons are characterized by ultra-high-field (28.2 T) 1H and 13C NMR spectroscopies to establish their molecular structures and resolve different stereoisomers, showing the utility of state-of-the-art spectroscopic tools for resolving structures of branched alkanes. Furthermore, the molecular-level diffusion and bulk viscosity properties compare favorably to classical synthetic lubricants based on hydrogenated polyalphaolefin blends, establishing olefin metathesis as a selective and scalable route to high-performance lubricant oils with defined molecular structures.

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