14035-81-5Relevant academic research and scientific papers
Synthesis of d-labeled and unlabeled ethyl succinic anhydrides and application to quantitative analysis of peptides by isotope differential mass spectrometry
Niwayama, Satomi,Zabet-Moghaddam, Masoud,Kurono, Sadamu,Kattanguru, Pullaiah,Shaikh, Aarif L.
, p. 5073 - 5077 (2016)
Ethyl succinic anhydride and its d5-labeled version have been synthesized and applied to quantitative analysis of peptides in combination with MALDI or ESI mass spectrometry. These modifiers react with amino groups in the N-termini and lysine side chains in proteins, and therefore the combination of these modifiers was shown to be a useful tool for quantification of peptides and hence for proteomics research.
Synthesis of Cyclic Anhydrides via Ligand-Enabled C–H Carbonylation of Simple Aliphatic Acids
Herron, Alastair N.,Yu, Jin-Quan,Zhuang, Zhe
supporting information, p. 16382 - 16387 (2021/06/23)
The development of C(sp3)–H functionalizations of free carboxylic acids has provided a wide range of versatile C?C and C?Y (Y=heteroatom) bond-forming reactions. Additionally, C–H functionalizations have lent themselves to the one-step preparation of a number of valuable synthetic motifs that are often difficult to prepare through conventional methods. Herein, we report a β- or γ-C(sp3)–H carbonylation of free carboxylic acids using Mo(CO)6 as a convenient solid CO source and enabled by a bidentate ligand, leading to convenient syntheses of cyclic anhydrides. Among these, the succinic anhydride products are versatile stepping stones for the mono-selective introduction of various functional groups at the β position of the parent acids by decarboxylative functionalizations, thus providing a divergent strategy to synthesize a myriad of carboxylic acids inaccessible by previous β-C–H activation reactions. The enantioselective carbonylation of free cyclopropanecarboxylic acids has also been achieved using a chiral bidentate thioether ligand.
Succinic anhydrides from epoxides
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Page/Page column 21; 22; 23, (2013/07/25)
Catalysts and methods for the double carbonylation of epoxides are disclosed. Each epoxide molecule reacts with two molecules of carbon monoxide to produce a succinic anhydride. The reaction is facilitated by catalysts combining a Lewis acidic species with a transition metal carbonyl complex. The double carbonylation is achieved in single process by using reaction conditions under which both carbonylation reactions occur without the necessity of isolating or purifying the product of the first carbonylation.
Catalytic double carbonylation of epoxides to succinic anhydrides: Catalyst discovery, reaction scope, and mechanism
Rowley, John M.,Lobkovsky, Emil B.,Coates, Geoffrey W.
, p. 4948 - 4960 (2008/02/03)
The first catalytic method for the efficient conversion of epoxides to succinic anhydrides via one-pot double carbonylation is reported. This reaction occurs in two stages: first, the epoxide is carbonylated to a β-lactone, and then the β-lactone is subsequently carbonylated to a succinic anhydride. This reaction is made possible by the bimetallic catalyst [(CITPP)Al(THF)2]+[Co(CO)4]- (1; CITPP = meso-tetra(4-chlorophenyl)porphyrinato; THF = tetrahydrofuran), which is highly active and selective for both epoxide and lactone carbonylation, and by the identification of a solvent that facilitates both stages. The catalysis is compatible with substituted epoxides having aliphatic, aromatic, alkene, ether, ester, alcohol, nitrile, and amide functional groups. Disubstituted and enantiomerically pure anhydrides are synthesized from epoxides with excellent retention of stereochemical purity. The mechanism of epoxide double carbonylation with 1 was investigated by in situ IR spectroscopy, which reveals that the two carbonylation stages are sequential and non-overlapping, such that epoxide carbonylation goes to completion before any of the intermediate β-lactone is consumed. The rates of both epoxide and lactone carbonylation are independent of carbon monoxide pressure and are first-order in the concentration of 1. The stages differ in that the rate of epoxide carbonylation is independent of substrate concentration and first-order in donor solvent, whereas the rate of lactone carbonylation is first-order in lactone and inversely dependent on the concentration of donor solvent. The opposite solvent effects and substrate order for these two stages are rationalized in terms of different resting states and rate-determining steps for each carbonylation reaction.
Estrogen receptor ligands. Part 9: Dihydrobenzoxathiin SERAMs with alkyl substituted pyrrolidine side chains and linkers
Blizzard, Timothy A.,Dininno, Frank,Morgan II, Jerry D.,Chen, Helen Y.,Wu, Jane Y.,Kim, Seongkon,Chan, Wanda,Birzin, Elizabeth T.,Yang, Yi Tien,Pai, Lee-Yuh,Fitzgerald, Paula M.D.,Sharma, Nandini,Li, Ying,Zhang, Zhoupeng,Hayes, Edward C.,Dasilva, Carolyn A.,Tang, Wei,Rohrer, Susan P.,Schaeffer, James M.,Hammond, Milton L.
, p. 107 - 113 (2007/10/03)
A series of benzoxathiin SERAMs was prepared. Minor modifications in the side chain or linker resulted in significant effects on biological activity, especially in uterine tissue. A series of dihydrobenzoxathiin SERAMs with alkylated pyrrolidine side chains or alkylated linkers was prepared. Minor modifications in the side chain or linker resulted in significant effects on biological activity, especially in uterine tissue.
Mechanism of trialkylborane promoted adhesion to low surface energy plastics
Sonnenschein, Mark F.,Webb, Steven P.,Kastl, Patrick E.,Arriola, Daniel J.,Wendt, Benjamin L.,Harrington, Daniel R.,Rondan, Nelson G.
, p. 7974 - 7978 (2007/10/03)
Excellent adhesion to low surface energy substrates such as polypropylene, polyethylene, poly(vinyl difluoride), and poly(tetrafluoroethylene) is obtained with acrylic polymerization initiated by trialkylboranes at room temperature and without need for surface pretreatment. The mechanism of adhesion is a consequence of a series of radical processes resulting from the initial oxidation of the trialkylborane followed by the production of alkoxy and alkyl radicals. This paper will elucidate the mechanism of adhesion using both experiment and theory.
Catalytic carbonylation of β-lactones to succinic anhydrides
Getzler, Yutan D. Y. L.,Kundnani, Vinod,Lobkovsky, Emil B.,Coates, Geoffrey W.
, p. 6842 - 6843 (2007/10/03)
A well-defined,highly active and selective catalyst for the synthesis of succinic anhydrides from CO and β-lactones is reported. At 200 psi of CO, the catalyst [(N,N′-bis(3,5-di-tert-butylsalicylidene)phenylenediamino)Al(THF)2][Co(CO)4] carbonylates β-propiolactones to succinic anhydrides in high yield. (R)-β-Butyrolactone is carbonylated to (S)-methylsuccinic anhydride with clean inversion of stereochemistry, while cis-2,3-dimethyl-β-propiolactone yields exclusively trans-2,3-dimethylsuccinic anhydride. These data are consistent with a mechanism involving nucleophilic attack by [Co(CO)4]- on the β carbon of the lactone, followed by CO insertion and anhydride formation. Copyright
Synthesis of monosubstituted succinic acids from tert-butylsuccinate
Bergmeier,Ismail
, p. 1369 - 1371 (2007/10/03)
We report the preparation and alkylation of the dianion of t-butylsuccinate. This alkylation reaction has proven to be a useful method for the preparation of monosubstituted succinic acids and anhydrides.
"ONE-POT" SYNTHESIS OF DISYMMETRICALLY α,α'-DISUBSTITUTED SUCCINIC ANHYDRIDES PRECURSORS
Dana, A.,Campagnole, M.,Bourgeois, M.J.,Montaudon, E.
, p. 2981 - 2988 (2007/10/03)
A "one-pot" synthesis for disymmetrically α,α'-disubstituted succinic anhydrides precursors isreported in the present paper.Substituents are aryl, primary or secondary alkyl groups.This reaction represents a simple and quick method with fair yields.
