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Cis-Norbornene-6-Endo-Dicarboxylic Anhydride

In contrast to their (oxa)norbornenyl counterparts, cyclobutenyl derivatives have been relatively unexplored in ring-opening metathesis polymerization (ROMP), despite the fact that ROMP of cyclobutene derivatives yields unsaturated polymers based on a strictly 1,4-polybutadiene backbone that is not easily accessible by other routes. This article provides a summary of our group's research on cyclobutenyl-capped macromonomers, which are useful building blocks for the synthesis of graft (bottle-brush) copolymers by ROMP through the so-called macromonomer (or grafting-through) approach. Synthetic strategies employing orthogonal chemistries such as reversible deactivation radical polymerization techniques (atom transfer radical polymerization ATRP and reversible addition-fragmentation chain transfert (RAFT) polymerization) and recent developments employing copper-catalyzed azidealkyne cycloaddition click chemistry are discussed. In addition, the ROMP of the produced macromonomers, as well as preliminary unique data on the ROMP of cyclobutenyl-capped macromonomers synthesized via RAFT polymerization and click chemistry, are described and discussed. Highlights of the graphical abstract Synthesis of cyclobutenyl compounds using ATRP, RAFT, and clickable moieties Synthesis of macromonomers with well-defined cyclobutenyl caps. ROMP of cyclobutenyl-capped macromonomers using a second-generation Grubbs catalyst.

Moles of maleic anhydride = mass / molar mass = 1 g / 98 g/ mol = 0 Therefore, the limiting reagent is maleic anhydride since it has less moles.Theoretical yield of cis-norbornene-5,6-endo-dicarboxylic anhydride(C 9 H 8 O 3): (0 mol x 164 g/ mol = 1 g Actual yield=

The purpose of this experiment is to produce cis-Norbornene-5,6-endo-Dicarboxylic anhydride by a Diels-alder reaction. Maleic anhydride and cyclohexadiene are the compounds employed. This experiment determines the melting point of cis-Norbornene-5,6-end-Dicarboxylic anhydride. Also, the yield percentage. Reaction: C5H6 + C4H2O3 C9H8O3 Equation of Reaction Physical data Structure Name Cyclopentadiene Maleic Anhydride Formula C5H6 C4H2O3 Molecular Weight 66.10g/mol 98.06g/mol Density 0.80g/mL 1.48g/mL Melting Point -86C 53C Boiling Point 42C 202C Mass Used 0.160g 0.205g Volume As the reaction was rinsed with hexane, the pipette may have removed the crystals, which might have contributed to the poor percentage yield. Another probable explanation is that crystals were left in the reaction tube when the reaction was transferred.

The melting point of cis-Norbornene-5, 6-endo-dicarboxylic anhydride is documented to be 165 degrees Celsius. 160- 163 degrees Celsius was the experimental result achieved using the Diels- Alder reaction. We were only able to get a 20.2% yield. A yield this low was unexpected, but it was sufficient to determine whether we had made cis-Norbornene-5, 6-endo-dicarboxylic anhydride by measuring the melting point. When cyclopentadiene is left out for a few days, the molecules slowly dimerize and form dicyclopentadiene. Dicyclopentadiene would not produce the necessary cis-Norbornene-5, 6-endo-dicarboxylic anhydride; hence, this must be corrected. In order to de-dimerize dicyclopentadiene, it must be heated to a temperature slightly below its boiling point. Our melting point is so close to the value reported in the literature for cis-Norbornene-5, 6-endo-dicarboxylic anhydride that it is quite probable that the intended product was achieved.

Cis-Norbornene-5 6-Endo-Dicarboxylic Anhydride Melting Point

On human hepatocellular carcinoma cells, the therapeutic benefits of cantharidin analogues without bridging ether oxygen were examined. Eur. J. Med. Chem. 45, 3981-5, (2010) Previous study reveals that cantharidin, norcantharidin, and its analogues inhibit cancer cell lines such as HL60, HT29, and L1210. Anticancer drugs...

The more hindered endo product is created and understood with the assistance of molecular orbital theory, which explains that the overlap of the p orbitals on the dienophile's substituents with the p orbitals on the diene is favorable and helps to bring the two molecules together. Frequently, an exo isomer will be separated from a Diels-Alder process, even if the endo product is first generated. This happens because the exo isomer, which has less steric strain than the endo isomer, is more stable and the Diels-Alder reaction is often reversible under reaction circumstances. Note that the diene and dienophile are on parallel planes and that the diene performs syn addition with the dienophile. Consequently, cis groups present in the dienophile are likewise present in the result. The experiment had a favorable outcome, with the production of a white crystal resembling a plate. The melting point of the crystal was between 158 and 160 degrees, which is close to the literature value. This little discrepancy in melting point is due to a trace quantity of contaminants. This may be the result of human mistake.

Mechanism:The Diels-Alder reaction has significant synthetic usefulness for the synthesis of unsaturated 6-membered rings (Kahn, 2011). The reaction will proceed at a higher rate if the reactants include more electron-attracting components. Due to the presence of several electronegative oxygen atoms in both cyclopentadiene and maleic anhydride, the reaction occurs relatively fast.

Cis-Norbornene-5 6-Endo-Dicarboxylic Anhydride Boiling Point

The melting point of cis-Norbornene-5, 6-endo-dicarboxylic anhydride is documented to be 165 degrees Celsius. 160- 163 degrees Celsius was the experimental result achieved using the Diels- Alder reaction. We were only able to get a 20.2% yield. A yield this low was unexpected, but it was sufficient to determine whether we had made cis-Norbornene-5, 6-endo-dicarboxylic anhydride by measuring the melting point. When cyclopentadiene is left out for a few days, the molecules slowly dimerize and form dicyclopentadiene. Dicyclopentadiene would not produce the necessary cis-Norbornene-5, 6-endo-dicarboxylic anhydride; hence, this must be corrected. In order to de-dimerize dicyclopentadiene, it must be heated to a temperature slightly below its boiling point. Our melting point is so close to the value reported in the literature for cis-Norbornene-5, 6-endo-dicarboxylic anhydride that it is quite probable that the intended product was achieved.

On human hepatocellular carcinoma cells, the therapeutic benefits of cantharidin analogues without bridging ether oxygen were examined. Eur. J. Med. Chem. 45, 3981-5, (2010) Previous study reveals that cantharidin, norcantharidin, and its analogues inhibit cancer cell lines such as HL60, HT29, and L1210. Anticancer drugs...

Cis-Norbornene-5 6-Endo-Dicarboxylic Anhydride Nmr

In refluxing carbon tetrachloride, benzenesulfonyl azide interacts with cis-endo (Ia) and cis-exo-norbornene-5,6-dicarboxylic anhydrides (IIa) and with the corresponding cis-exo-dimethyl ester (IIb) to produce mostly endo aziridines. Under similar circumstances, the cis-endo dimethyl ester (Ib) produces the exo aziridine solely, while under photolytic conditions, the cis-exo and cis-endo anhydrides and dimethyl esters produce virtually exclusively exo aziridines. The cis-exo dimethyl ester IIb yields largely the exo aziridine at room temperature, while p-methoxybenzenesulfonyl azide interacts with the endo-anhydride Ia in refluxing carbon tetrachloride to produce an even bigger proportion of the endo aziridine. On pyrolysis in decalin, the exo-1,2,3-2-triazoline XIIIa prepared from the exo anhydride and phenyl azide yields an almost 1:1 ratio of the exo and endo aziridine.A proposed mechanism involves the conversion of exo-1,2,3-2-triazolines to endo aziridines via a 3-diazomethylcyclopentane-2-carboxaldehydeimine intermediate (XI).

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