1228236-04-1

Basic information

• Product Name: C₁₃H₁₆⁽²⁾H₄O₄
• Synonyms: C₁₃H₁₆⁽²⁾H₄O₄
• CAS NO: 1228236-04-1
• Molecular Weight: 244.268
• Mol File: 1228236-04-1.mol

Chemical Properties

• CAS DataBase Reference: C₁₃H₁₆⁽²⁾H₄O₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₃H₁₆⁽²⁾H₄O₄(1228236-04-1)
• EPA Substance Registry System: C₁₃H₁₆⁽²⁾H₄O₄(1228236-04-1)

Safety Data

• Hazardous Substances Data: 1228236-04-1(Hazardous Substances Data)

Upstream product

• 1228236-01-8 C₁₃H₁₈⁽²⁾H₂O₄ 

Relevant articles and documents

Exploiting and understanding the selectivity of Ru-N-Heterocyclic carbene metathesis catalysts for the ethenolysis of cyclic olefins to α,ω-Dienes

A library of 29 homologous Ru-based olefin metathesis catalysts has been tested for ethenolysis of cyclic olefins toward the goal of selectively forming α,ω-diene using cis-cyclooctene as a prototypical substrate. Dissymmetry at the N-heterocyclic carbene (NHC) ligand was identified as a key parameter for controlling the selectivity. The best-performing catalyst bearing an N-CF3 group significantly outperformed the benchmark second-generation Grubbs catalyst in the ethenolysis of cis-cyclooctene. Application of this optimal catalyst to the ethenolysis of various norbornenes allows the efficient synthesis of valuable diene intermediates in good yields. The observed ligand effect trends could be rationalized through univariate and multivariate parameter analysis involving steric and electronic descriptors of the NHC ligand in the form of the buried volume and the 77Se NMR chemical shift, in particular the σyy component of the shielding tensor of [Se(NHC)] model compounds, respectively. Natural chemical shift analysis of this chemical shielding tensor shows that σyy probes the I-Acceptor property of the NHC ligand, the essential electronic parameter that drives the relative rate of degenerate metathesis and selectivity in ethenolysis with catalysts bearing dissymmetric NHC ligands.

Correction: Exploiting and understanding the selectivity of Ru-N-heterocyclic carbene metathesis catalysts for the ethenolysis of cyclic olefins to α,ω-Dienes (Journal of the American Chemical Society (2017) 139:37 (13117-13125) DOI: 10.1021/jacs.7b06947)

The isotropic chemical shielding (iso) was mislabeled as the isotropic chemical shift (iso) in Table S40, Figures 2, 4, S153 and in the respective discussion of these figures in the text. The corrected figures are shown below; the SI graphics are provided in the corrected SI file. In the conclusion section, "cyclic olefins" was incorrectly written as "cyclic dienes" to be the essential structural feature for the selective ethenolysis toward w-dienes. The ROMP activity of Ru-20 is not detectable in the "presence of ethylene"; this was incorrectly written as the "absence of ethylene". Equations 5 and 7, pages S47 and S135 respectively, had errors that have been fixed in the corrected SI file. None of the above affects any conclusions of the article. (Figure Presented).

Nonproductive events in ring-closing metathesis using ruthenium catalysts

The relative TONs of productive and nonproductive metathesis reactions of diethyl diallylmalonate are compared for eight different ruthenium-based catalysts. Nonproductive cross metathesis is proposed to involve a chain-carrying ruthenium methylidene. A second more-challenging substrate (dimethyl allylmethylallylmalonate) that forms a trisubstituted olefin product is used to further delineate the effect of catalyst structure on the relative efficiencies of these processes. A steric model is proposed to explain the observed trends.