Chemistry of Heterocyclic Compounds

, Volume 54, Issue 4, pp 403–410 | Cite as

Aromatization of 2,2,5-trialkyl-substituted 2,5-dihydrofurans and factors affecting their stabilization

  • Bulat T. Sharipov
  • Anna N. Davidova
  • Farid A. Valeev
Article
  • 3 Downloads

We demonstrate that the synthesis of 5-methoxy-2,2,5-trialkyl-substituted 2,5-dihydrofurans containing unprotected hydroxymethyl group at the C-2 position involves aromatization via fragmentation involving С–С bond cleavage, resulting in the formation of 2,5-disubstituted furans and carbonyl compounds. 2,5-Dihydrofurans bearing an ester group at the С-2 position were stable. It was found that 2,2,5-trialkyl-substituted 2,5-dihydrofurans containing a hydroxymethyl or carbonyl group in the side chain could aromatize through auto-oxidation, which was facilitated by adjacent functional groups (sulfo- or pivaloyl groups).

Keywords

2,5-dihydrofurans 2,5-disubstituted furans aromatization auto-oxidation fragmentation 

Notes

This work was performed according to State contract (АААА-А17-117011910022-5) and with financial support from the Russian Foundation for Basic Research (grant 17-43-020166 r_a) and the President of Russian Federation award for young scientists (SP-1934.2015.4).

Spectral analyses were performed on the equipment of Collective Use Center “Chemistry” at the Ufa Institute of Chemistry, Ufa Research Center of the Russian Academy of Sciences.

Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Bulat T. Sharipov
    • 1
  • Anna N. Davidova
    • 1
  • Farid A. Valeev
    • 1
  1. 1.Ufa Institute of ChemistryUfa Research Center of the Russian Academy of SciencesUfaRussia

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