5405-41-4Relevant articles and documents
Reaction of ethyl 2,2-dimethoxycyclopropanecarboxylates with m-CPBA. Discovery of two new related degradative processes leading to β-hydroxyacid derivatives
Piccialli, Vincenzo,Graziano, M. Liliana
, p. 93 - 95 (2001)
The reaction of the 3-alkyl-substituted and 3,3-dialkyl-substituted ethyl 2,2-dimethoxycyclopropanecarboxylates 1-3 with m-CPBA in CH2Cl2 leads to the formation of the β-hydroxyacid derivatives 4-6 via two related processes involving the scission of both the C1-C2 and C2-C3 bonds and consequently to the degradation of the original cyclopropane carbon skeleton (extrusion of the C-2 carbon). Cis- and trans-2-ethoxycyclopropanecarboxylic acid ethyl esters 9 and 10, respectively, structurally related to 1-3, are unreactive under the same conditions. A hypothesis explaining the observed reactivity is formulated.
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Lease,McElvain
, p. 806 (1933)
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Synthesis, Structure, and Catalytic Hydrogenation Activity of [NO]-Chelate Half-Sandwich Iridium Complexes with Schiff Base Ligands
Lv, Wen-Rui,Li, Rong-Jian,Liu, Zhen-Jiang,Jin, Yan,Yao, Zi-Jian
, p. 8181 - 8188 (2021/05/26)
A series of N,O-coordinate iridium(III) complexes with a half-sandwich motif bearing Schiff base ligands for catalytic hydrogenation of nitro and carbonyl substrates have been synthesized. All iridium complexes showed efficient catalytic activity for the hydrogenation of ketones, aldehydes, and nitro-containing compounds using clean H2 as reducing reagent. The iridium catalyst displayed the highest TON values of 960 and 950 in the hydrogenation of carbonyl and nitro substrates, respectively. Various types of substrates with different substituted groups afforded corresponding products in excellent yields. All N,O-coordinate iridium(III) complexes 1-4 were well characterized by IR, NMR, HRMS, and elemental analysis. The molecular structure of complex 1 was further characterized by single-crystal X-ray determination.
Concise Synthesis of (+)-[13C4]-Anatoxin-a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion
Chen, Karen Y.,Lacharity, Jacob J.,Mailyan, Artur K.,Zakarian, Armen
supporting information, p. 11364 - 11368 (2020/05/18)
An asymmetric total synthesis of [13C4]-anatoxin-a ([13C4]-1) has been developed from commercially available ethyl [13C4]-acetoacetate ([13C4]-15). The unique requirements associated with isotope incorporation inspired a new, robust, and highly scalable route, providing access to 0.110 g of this internal standard for use in the detection and precise quantification of anatoxin-a in freshwater. A highlight of the synthesis is a method that leverages a cyclic iminium ion racemization to achieve dynamic kinetic resolution in an enantioselective Morita–Baylis–Hillman (MBH) cyclization.
Catalytic hydrogenation of carbonyl and nitro compounds using an [: N, O] -chelate half-sandwich ruthenium catalyst
Yao, Zi-Jian,Zhu, Jing-Wei,Lin, Nan,Qiao, Xin-Chao,Deng, Wei
, p. 7158 - 7166 (2019/06/13)
A series of N,O-chelate half-sandwich ruthenium complexes for both carbonyl and nitro compound hydrogenation have been synthesized based on β-ketoamino ligands. All complexes exhibited high activity for the catalytic hydrogenation of a series of ketones and nitroarenes with molecular H2 as the reducing reagent in aqueous medium. Consequently, the catalytic system showed the catalytic TON values of 950 for 1-phenylethanol in acetophenone hydrogenation and 1960 for 1-chloro-4-nitrobenzene in p-chloroaniline hydrogenation. Good catalytic activity was displayed for various kinds of substrates with either electron-donating or electron-withdrawing groups. The neutral ruthenium complexes 1-4 were fully characterized using NMR, IR, and elemental analysis. Molecular structures of complexes 2 and 4 were further confirmed using single-crystal X-ray diffraction analysis.
