Cas: 14166-28-0 | Polonski, Tadeuszpublished an article in 1993

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Category: tetrahydrofurans It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Polonski, Tadeusz;Milewska, Maria J.;Gdaniec, Maria;Gilski, Miroslaw published 《Molecular geometry and circular dichroism spectra of bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydrides and imides》 in 1993. The article was appeared in 《Journal of Organic Chemistry》. They have made some progress in their research.Category: tetrahydrofurans The article mentions the following:

Several tricyclic anhydrides and imides derived from optically active bicyclo[2.2.1]heptane-2,3-dicarboxylic acids were synthesized, and their CD spectra are reported. On the basis of MNDO calculations it was estimated that despite rigidity of the norbornane system, the five-membered rings of succinic anhydride and imide moieties are slightly twisted. The chromophores are flexible and can be more or less skewed depending on solvent polarity. The chromophore nonplanarity significantly influences magnitude and sign of the first Cotton effect associated with the lowest energy n-π* electronic transition. The sign of the second n-π* Cotton effect is governed by vicinal effect of substituents. The crystal structures of three N-(S)-1-phenylethylimides were solved to estimate the configuration of C-2 of the imide moieties.(3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) were involved in the experimental procedure.

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Category: tetrahydrofurans It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Explore more uses of cas: 14166-28-0 | Journal of the American Chemical Society

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Application In Synthesis of (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Bercot, Eric A.;Rovis, Tomislav published 《Highly Efficient Nickel-Catalyzed Cross-Coupling of Succinic and Glutaric Anhydrides with Organozinc Reagents》 in 2005. The article was appeared in 《Journal of the American Chemical Society》. They have made some progress in their research.Application In Synthesis of (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione The article mentions the following:

A nickel-catalyzed alkylation of succinic and glutaric anhydrides with alkyl- and arylzinc reagents has been developed. A dramatic olefin effect has been investigated resulting in the identification of several styrene-based promoters which show pronounced enhancements in reaction rate. The substrate scope with respect to electrophilic and nucleophilic coupling partners has been examined and found to be remarkably broad, allowing for rapid introduction of mol. complexity through the use of functionalized coupling partners. Regioselective alkylation of an unsym. succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event. To complete the study, the researchers used (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Application In Synthesis of (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Zhou, Zheng-Hong et al. published new experimental results with the assistance of cas: 14166-28-0

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Formula: C9H10O3《Synthesis of glycerophospholipid conjugates of cantharidin and its analogues》 was published in 2000. The authors were Zhou, Zheng-Hong;Chen, Ru-Yu, and the article was included in《Synthetic Communications》. The author mentioned the following in the article:

A series of glycerophospholipid conjugates of cantharidin and its analogs were synthesized in a one-pot reaction, using hexaethylphosphorus triamide, activated by a catalytic amount of iodine, as the phosphorylating reagent. The structures of the title compounds were confirmed by 1H NMR, 31P NMR, IR and elemental anal. And (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) was used in the research process.

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Csende, Ferenc et al. published new progress in experiments with the help of cas: 14166-28-0

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Csende, Ferenc;Stajer, Geza published 《A convenient reduction of unsaturated bicyclic anhydrides》. The research results were published in《Organic Preparations and Procedures International》 in 1999.COA of Formula: C9H10O3 The article conveys some information:

Bicyclic anhydrides such as I are hydrogenated in 89-98% yields to saturated bicyclic anhydrides such as II by using cyclohexene as a transfer hydrogenation substrate in the presence of palladium on carbon. E.g., I dissolved in THF is treated with 2 equivalent of cyclohexene in the presence of palladium on carbon and refluxed for 8-12 h to give II in 98% yield. The modified procedure avoids the use of flammable reagents such as Raney nickel or mol. hydrogen. The experimental procedure involved many compounds, such as (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

McCluskey, Adam et al. published new progress in experiments with the help of cas: 14166-28-0

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

COA of Formula: C9H10O3In 1996, McCluskey, Adam;Taylor, Cherie;Quinn, Ronald J.;Suganuma, Masami;Fujiki, Hirota published 《Inhibition of protein phosphatase 2A by cantharidin analogs》. 《Bioorganic & Medicinal Chemistry Letters》published the findings. The article contains the following contents:

The syntheses of several cantharidin analogs and their biochem. effects on protein phosphatase 2A are described. Comparison of the PP2A inhibition of these cantharidin analogs has shown that the 7-oxo moiety and the anhydride system contribute to the biochem. activity. The diacid forms of several anhydrides showed reduced inhibition of PP2A. To complete the study, the researchers used (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Explore more uses of cas: 14166-28-0 | Green Chemistry

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Formula: C9H10O3《Metal-free, regioselective and stereoregular alternating copolymerization of monosubstituted epoxides and tricyclic anhydrides》 was published in 2018. The authors were Ji, He-Yuan;Chen, Xiao-Lu;Wang, Bin;Pan, Li;Li, Yue-Sheng, and the article was included in《Green Chemistry》. The author mentioned the following in the article:

A metal-free, highly regioselective and stereoregular ring-opening alternating copolymerization (ROAC) of monosubstituted epoxides with tricyclic anhydrides remains a challenge in the advancement of polyester synthesis. Herein, we described an effective group of organic dual catalysts for the ROAC, exhibiting a high catalytic activity (the highest TOF = 330 h-1 at 110°), narrow polydispersity (PDI <1.20) and excellent alternating selectivity (ester >99%) in a controlled manner. The ROAC of a variety of monosubstituted epoxides and tricyclic anhydrides was carried out under mild conditions. Of importance is the fact that highly regioselective insertion of epoxides has been realized by simple and metal-free catalysts in the ROAC, where the highest regioselectivity is up to 98% for aliphatic epoxides and glycidyl ethers at 80°. Styrene oxide bearing electron-withdrawing Ph also showed a good regioselectivity of 78%. Besides, the complete suppression of epimerization and transesterification was achieved even at high conversion for a variety of tricyclic anhydrides. Furthermore, block and gradient copolymers were synthesized by the sequential addition strategy and one-pot terpolymn. Accordingly, a green, regioselective and stereoregular fabrication of functional polyesters was realized for the first time by a metal-free process. The experimental procedure involved many compounds, such as (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

New progress of cas: 14166-28-0 | ACS Catalysis 2021

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.HPLC of Formula: 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Besalu-Sala, Pau;Sola, Miquel;Luis, Josep M.;Torrent-Sucarrat, Miquel published 《Fast and Simple Evaluation of the Catalysis and Selectivity Induced by External Electric Fields》 in 2021. The article was appeared in 《ACS Catalysis》. They have made some progress in their research.HPLC of Formula: 14166-28-0 The article mentions the following:

In the oriented external elec.-field-driven catalysis, the reaction rates and the selectivity of chem. reactions can be tuned at will. The activation barriers of chem. reactions within external elec. fields of several strengths and directions can be computationally modeled. However, the calculation of all of the required field-dependent transition states and reactants is computationally demanding, especially for large systems. Herein, we present a method based on the Taylor expansion of the field-dependent energy of the reactants and transition states in terms of their field-free dipole moments and elec. (hyper)polarizabilities. This approach, called field-dependent energy barrier (FDBβ), allows systematic one-dimensional (1D), two-dimensional (2D), and three-dimensional (3D) representations of the activation energy barriers for any strength and direction of the external elec. field. The calculation of the field-dependent FDBβ energy barriers has a computational cost several orders of magnitude lower than the explicit elec. field optimizations, and the errors of the FDBβ barriers are within the range of only 1-2 kcal·mol-1. The achieved accuracy is sufficient for a fast-screening tool to study and predict potential elec.-field-induced catalysis, regioselectivity, and stereoselectivity. As illustrative examples, four cycloadditions (1,3-dipolar and Diels-Alder) are studied. To complete the study, the researchers used (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.HPLC of Formula: 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Learn more about cas: 14166-28-0 | Bulletin of the College of Science, University of Baghdad 1967

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

COA of Formula: C9H10O3《Nuclear magnetic resonance spectroscopy. Establishment of configuration in Diels-Alder adducts》 was published in 1967. The authors were Sarkis, George Y., and the article was included in《Bulletin of the College of Science, University of Baghdad》. The author mentioned the following in the article:

The presence of the double bond shifted the absorption downfield for both exo- and endo-protons in dehydronorbornyl and norbornyl acids, acid chlorides, anhydrides, and nitriles. The magnitude of this shift is very small for the endo-proton (of the exo-epimer). When both epimers are available, a differentiation can be made by the fact that the exo-protons absorb at lower field than the endo-protons. And (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) was used in the research process.

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem