ALTERNATIVE METHOD FOR SYNTHESIS OF TETRACARBOXYLIC ACIDS WITH CYCLOALIPHATIC FRAGMENTS
Abstract and keywords
Abstract (English):
The tetracarboxylic acids containing a cycloaliphatic fragment are promising monomers for semi-aromatic polymers of a series of polyimides, polyesters, and polyetherimides. An alternative method has been developed for their synthesis. The method demonstrates the possibility of performing alkylation and acylation reactions in sequence. The choice of the combination of methods for the oxidation of the acyl and methyl groups has been confirmed by quantum chemical calculations.

Keywords:
Friedel-Crafts alkylation, tetracarboxylic acids, cycloaliphatic fragment
Text
Text (PDF): Read Download
References

1. Mi M.-C., Szu F.-E., Cheng Y.-C., Tsai C.-H., Chen J.-H., Huang, J.-H. Kuo, C.-C., Lin Y.-C., Leung M.-K., Chen W.-C. Semi-aromatic copolymers of poly (ether imide) with alicyclic diamines for obtaining low oxidation properties at a high frequency of 10-40 GHz. Appl. Polym. Mater., 2024, 6(18), 11137–11148. DOI:https://doi.org/10.1021/acsapm.4c01405 EDN: https://elibrary.ru/LLJCVB

2. Sachs J.D., Tonks I.A. Synthesis of poly(ether-ether) polymers by hydroesterification polymerization of α,ω enol esters. Macromolecules, 2022, 55(21), 9520–9526. DOI:https://doi.org/10.1021/acs.macromol.2c01935 EDN: https://elibrary.ru/YSFIOX

3. Wang D.H., Lee K.M., Lee D.H., Bachkowski M., Park H., MccOnnie M.E., Tan L.-S. The role of alicyclic conformational isomerization in the photomechanical characteristics of crosslinked polyimides with azobenzene functional groups containing tetrasubstituted cyclohexane fragments. ACS Macro Letters, 2021, 10(2), 278–283. DOI:https://doi.org/10.1021/acsmacrolett.0c00903 EDN: https://elibrary.ru/GMIMGS

4. Hosseini N.E., van Melis K.G.V., Vermeer T.J., Koning K.E., Duchateau R. Polymerization of cyclohexenoxide and anhydrides with alternating cycle opening: the effect of the catalyst, co-catalyst, and anhydride structure. Macromolecules, 2012, 45(4), 1770-1776. DOI:https://doi.org/10.1021/ma2025804

5. Nagura M., Sakurazawa M., Suzuki R. Pat.US № 2015346390, 2015.

6. Hatanaka T., Adachi I. Pat. KR № 20120000104, 2012.

7. Nakahata M. Pat. JP № 2011142393, 2011

8. Yang A., Xu C. Synthesis and Characterization of a Polyimide-Epoxy Composite for Dental Applications. Mech. Compos. Mater., 2018, 54(1), 71–78. DOIhttps://doi.org/10.1007/s11029-018-9719-7. EDN: https://elibrary.ru/SOQRZQ

9. Li H.T., Lin M.S., Chuang H.R. Wang, M.-W. Siloxane- and Imide-modified Epoxy Resin Cured with Siloxane-containing Dianhydride. J. Polym. Res., 2005, 12(5), 385–391. DOI:https://doi.org/10.1007/s10965-005-1766-9

10. Tachibana Y., Tsutsuba T., Sakata Ms., Kasuya K.-I. Disubstituted cyclohexane monomers as biodegradable building block: Evaluation of biodegradability of polyesters containing cyclohexane ring. Polym. Degrad. Stab., 2023, 217, 110516.DOI:https://doi.org/10.1016/j.polymdegradstab.2023.110516. EDN: https://elibrary.ru/SNVTUE

11. Unoh Y., Satoh T., Hirano K., Miura M. Rhodium(III)-Catalyzed Direct Coupling of Arylphosphine Derivatives with Heterobicyclic Alkenes: A Concise Route to Biarylphosphines and Dibenzophosphole Derivatives. ACS Catalysis, 2015, 5, 6634–6639. DOIhttps://doi.org/10.1021/acscatal.5b01896

12. Madan S., Cheng C.H. Nickel-catalyzed synthesis of benzocoumarins: application to the total synthesis of arnottin I. J. Org. Chem., 2006,71(21), 8312-5. DOI:https://doi.org/10.1021/jo061477h.

13. Adak L., Jin M., Saito S., Kawabata T., Itoh T., Ito S., Sharma A.K., Gower N.J., Cogswell P., Geldsetzer J., Takaya H., Isozaki K., Nakamura M. Iron-catalysed enantioselective carbometalation of azabicycloalkenes. ChemCommun (Camb), 2021, 57(57), 6975-6978. DOI:https://doi.org/10.1039/d1cc02387j EDN: https://elibrary.ru/TASOUL

14. Boon-Hong T. Cobalt-Catalyzed Addition of Arylzinc Reagents to Norbornene Derivatives through 1,4 Cobalt Migration.Org.Lett., 2014, 16(12), 3392–3393. DOI:https://doi.org/10.1021/ol501449j

15. Lin Q., Yang W., Yao Y., Chen S., Tan Y., Chen D., Yang D. Copper-Catalyzed Diastereoselective 1,2 Difunctionalization of Oxabenzonorbornadienes Leading to β-Thiocyanato Thioethers. Org Lett., 2019, 21(18), 7244-7247. DOI:https://doi.org/10.1021/acs.orglett.9b02452. EDN: https://elibrary.ru/CXXSUW

16. Magnus R.A. Review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis. BeilsteinJ.Org. Chem., 2010, 6(6),6–11. DOI:https://doi.org/10.3762/bjoc.6.6

17. Firstova A.A., KofanovE.R., Krasovskaya G.G., Danilova A.S. Simple and efficient synthesis of new tricarboxylic acids bearing cyclohexane and norbornane fragments. Russ. Chem. Bull., 2017, 66, 867–869. DOI:https://doi.org/10.1007/s11172-017-1820-x EDN: https://elibrary.ru/XNRLCR

18. Firstova A.A., Kofanov E.R. Synthesis of Phenylcycloalkanepolycarboxylic Acids. Russ. J. Org. Chem., 2023, 59, 820–825 DOI:https://doi.org/10.31857/S0514749223050129 DOI: https://doi.org/10.1134/s1070428023050123; EDN: https://elibrary.ru/LCWOWV

19. Kamiya Y., Kashima M. The autoxidation of aromatic hydrocarbons catalyzed with cobaltic acetate in acetic acid solution: I. The oxidation of toluene. J. Catal., 1972, 25(3), 326-333.DOIhttps://doi.org/10.1016/0021-9517(72)90234-5

20. Becke A.D. A new mixing of Hartree-Fock and local density-functional theories. J. Chem. Phys.,1993,98, 1372 1377. DOIhttps://doi.org/10.1063/1.464304

21. Flurry R.L. Quantum chemistry: An introduction. NJ: Prentice-Hall, Inc., 1983. 399pp.

22. Parr R.G., Szentpalyand L.V., Liu S. Electrophilicity Index.J. Am. Chem. Soc., 1999, 121, 1922. DOI:https://doi.org/10.1021/ja983494x

23. Ignatov S.K. Kvantovo-khimicheskoye modelirovaniye atomno-molekulyarnykh protsessov. Nizhniy Novgorod: NGU im. N. I. Lobachevskogo, 2019, 93 s. (in Russian).

24. Plekhovich S.D., Zelentsov S.V. Raschet perekhodnykh sostoyaniy metodami kvantovoy khimii. Uchebno-metodicheskoye posobiye. Nizhniy Novgorod: Nizhegorodskiy gosuniversitet, 2015, 21 s. (in Russian).

Login or Create
* Forgot password?