Functional derivatization of 3- and 5-substituted cyclooctenes

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Abstract

New derivatives of cyclooctene with an ester group in the 3- and 5-positions have been synthesized in high yield. The structure of obtained compounds was confirmed by a complex of physicochemical methods. The products are of interest as monomers for the synthesis of hydrophilic and amphiphilic homo- and copolymers using ring-opening metathesis polymerization of olefins. Owing to the unsaturated backbone, such polymers can undergo further modification, including by the reaction of macromolecular cross-metathesis.

About the authors

O. A Adzhieva

A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: finko.alexander@gmail.com

A. V Finko

A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences;Moscow State University

Email: finko.alexander@gmail.com

A. V Roenko

A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: finko.alexander@gmail.com

Yu. I. Denisova

A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: finko.alexander@gmail.com

Y. V Kudryavtsev

A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: finko.alexander@gmail.com

References

  1. Andresen T.L., Skytte D.M., Madsen R. Org. Biomol. Chem. 2004, 2, 2951-2957. doi: 10.1039/B411021H
  2. Hughes D.L., Wheeler P., Ene D. Org. Process Res. Dev. 2017, 21, 1938-1962. doi: 10.1021/acs.oprd.7b00319
  3. Schuster M., Blechert S. Angew. Chem. Int. Ed. 1997, 36, 2036-2056. doi: 10.1002/anie.199720361
  4. Dragutan I., Dragutan V., Demonceau A. RSC Adv. 2012, 2, 719-736. doi: 10.1039/C1RA00910A
  5. Mol J.C. Green Chem. 2002, 4, 5-13. doi: 10.1039/B109896A
  6. Chikkali S., Mecking S. Angew. Chem. 2012, 51, 5802-5808. doi: 10.1002/anie.201107645
  7. Bilel H., Hamdi N., Fischmeister C., Bruneau C. ChemCatChem. 2020, 12, 5000-5021. doi: 10.1002/cctc.202000959
  8. Bielawski C.W., Grubbs R.H. Prog. Polym. Sci. 2007, 32, 1-29. doi: 10.1016/j.progpolymsci.2006.08.006
  9. Schrock R.R. Acc. Chem. Res. 2014, 47, 2457-2466. doi: 10.1021/ar500139s
  10. Sinclair F., Alkattan M., Prunet J., Shaver M.P. Polym. Chem. 2017, 8, 3385-3398. doi: 10.1039/C7PY00340D
  11. Leimgruber S., Trimmel G. Monatsh. Chem. 2015, 146, 1081-1097. doi: 10.1007/s00706-015-1501-0
  12. Binder J.B., Raines R.T. Curr. Opin. Chem. Biol. 2008, 12, 767-773. doi: 10.1016/j.cbpa.2008.09.022
  13. Martinez H., Ren N., Matta M.E., Hillmyer M.A. Polym. Chem. 2014, 5, 3507-3532. doi: 10.1039/c3py01787g
  14. Zhang K., Dou Y., Jiang Y., Zhang Z., Li Sh., Cui D. Macromolecules. 2021, 54, 9445-9451. doi: 10.1021/acs.macromol.1c01384
  15. Hillmyer M.A., Laredo W.R., Grubbs R.H. Macromolecules. 1995, 28, 6311-6316. doi: 10.1021/ma00122a043
  16. Han H., Chen F., Yu J., Dang J., Ma Z., Zhang Y., Xie M. J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 3986-3993. doi: 10.1002/pola.22152
  17. Maughon B.R., Grubbs R.H. Macromolecules. 1996, 29, 5765-5769. doi: 10.1021/ma960049i
  18. Demonceau A., Stumpf A.W., Saive E., Noels A.F. Macromolecules. 1997, 30, 3127-3136. doi: 10.1021/ma961040j
  19. Osawa K., Kobayashi S., Tanaka M. Macromolecules. 2016, 49, 8154-8161. doi: 10.1021/acs.macromol.6b01829
  20. Martinez H., Zhang J., Kobayashi S., Xu Y., Pitet L.M., Matta M.E., Hillmyer M.A. Appl. Petrochem. Res. 2015, 5, 19-25. doi: 10.1007/s13203-014-0048-z
  21. Kobayashi S., Fukuda K., Kataoka M., Tanaka M. Macromolecules. 2016, 49, 2493-2501. doi: 10.1021/acs.macromol.6b00273
  22. Denisova Y.I., Roenko A.V., Adzhieva O.A., Gringolts M.L., Shandryuk G.A., Peregudov A.S., Finkelshtein E.Sh., Kudryavtsev Y.V. Polym. Chem. 2020, 11, 7063-7077. doi: 10.1039/d0py01167c
  23. De Geus M.A.R., Groenewold G.J.M., Maurits E., Araman C., Van Kasteren S.I. Chem. Sci. 2020, 11, 10175-10179. doi: 10.1039/D0SC03216F
  24. Revanur R., McCloskey B., Breitenkamp K., Freeman B.D., Emrick T. Macromolecules. 2007, 40, 3624-3630. doi: 10.1021/ma0701033
  25. Breitenkamp R.B., Ou Z., Breitenkamp K., Muthukumar M., Emrick T. Macromolecules. 2007, 40, 7617-7624. doi: 10.1021/ma070714v
  26. Bailey F.E., Koleske J.V. Ullmann's Encyclopedia of Industrial Chemistry. 2000, 29, 355-365. doi: 10.1002/14356007.a21_579
  27. Bond C.W., Cresswell A.J., Davies S.G., Fletcher A.M., Kurosawa W., Lee J.A., Roberts P.M., Russell A.J., Smith A.D., Thomson J.E. J. Org. Chem. 2009, 74, 6735-6748. doi: 10.1021/jo9012783
  28. Ashby E.C., Coleman D. J. Org. Chem. 1987, 52, 4554-4565. doi: 10.1021/jo00229a023
  29. Breitenkamp K., Simeone J., Jin E., Emrick T. Macromolecules. 2002, 35, 9249-9252. doi: 10.1021/ma021094v
  30. Wang J-X., Ge W., Fu M-C., Fu Y. Org. Lett. 2022, 24, 1471-1475. doi: 10.1021/acs.orglett.1c04359

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