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Search for "CH acidity" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.
Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination
Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24
- equilibrium) under the action of an excess of nucleophiles as bases. Such dianions are characteristic of acenaphthene and have been repeatedly detected in subsequent transformations [18][19]. In our case, the CH-acidity of the CH2CH2 bridge should be even higher under the action of pyridine rings, and, if
Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?
Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61
- pathway. This, together with the height of the activation barriers for individual pathways and intermediates, explains the observed formation of different types of products. While salt 10a with a low barrier value for the ECR pathway and the highest CH acidity provides exclusively the ECR coupling product
Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones
Beilstein J. Org. Chem. 2019, 15, 1289–1297, doi:10.3762/bjoc.15.127
- ) complexes [56]. The above considerations lead to the use of β-ketosulfones in the Ni(II)-catalyzed reaction, since the proposed mechanism [47], that involves the formation of cyclic Ni enolate, and the high CH acidity of ketosulfones (pKa 9.8–10.5 [4]). The formation of the key intermediate can be provided
- organocatalysts [58][59][60][61]. This was explained by the authors as a result of the high CH acidity of the corresponding Michael adducts. The highest reaction rate with good enantioselectivity is achieved using catalyst 7a (Table 1, entry 1). For this reason, further studies were carried out with catalyst 7a
Halogen-containing thiazole orange analogues – new fluorogenic DNA stains
Beilstein J. Org. Chem. 2017, 13, 2902–2914, doi:10.3762/bjoc.13.283
- for the success of the reaction because of the CH-acidity of the benzyl fragment, which otherwise leads to the possibility of side reactions if trimethylamine or other less hindered basic reagents are employed. Photophysical properties Absorption The longest wavelength absorption maxima of the studied
Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship
Beilstein J. Org. Chem. 2015, 11, 1475–1485, doi:10.3762/bjoc.11.160
- using the DFT B3LYP method in order to rationalize the experimental results. Keywords: CH acidity; indoles; iodolysis; mixed lithium–zinc bases; pyrroles; Introduction Pyrrole occurs in very important natural products such as tetrapyrrolic (linear) bilirubinoids, and (cyclic) porphyrins and corrins
- recently [42][52]. The results of quantum chemical calculations on CH acidity of the different N-arylated pyrroles 1 and indoles 2, obtained both for THF solution (Figure 5) and gas phase (see Supporting Information File 1), are presented in the current paper. A potential acidity of the methoxy groups in
- weak CH acidic compounds while the pKa values in THF solution (Figure 5) covered a 28.8–45.0 span. These data allow the assignment of potential deprotonation sites in the investigated substrates. Also the correlation between gas-phase ΔGacid and the pKa(THF) values can be tracked. In all cases, the CH
Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones
Beilstein J. Org. Chem. 2012, 8, 1246–1255, doi:10.3762/bjoc.8.140
- steric strain. Due to the CH-acidity at the α-position of the formyl group, epimerization of the all-trans product 24 under acidic or basic conditions could be expected. Lange et al. reported the catalytic hydrogenation of a structurally close analogue, (5R)-1-formyl-2-methyl-5-isopropylcyclopent-1-ene
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