Non-Symmetrical Tetrafluoroalkadienes Synthesized by ROCM of 3,3,4,4-Tetrafluorocyclobutene

0571960 - ÚOCHB 2024 RIV DE eng J - Journal Article
Kučnirová, K. - Kvíčala, J. - Svoboda, Martin - Cvačka, Josef - Čejka, J. - Rybáčková, M.
Non-Symmetrical Tetrafluoroalkadienes Synthesized by ROCM of 3,3,4,4-Tetrafluorocyclobutene.
Chemistry - A European Journal. Roč. 29, č. 34 (2023), č. článku e202300435. ISSN 0947-6539. E-ISSN 1521-3765
Institutional support: RVO:61388963
Keywords : fluorine * fluoroalkene metathesis * metathesis * ring-opening cross metathesis * tetrafluorocyclobutene
OECD category: Analytical chemistry
Impact factor: 4.3, year: 2022
Method of publishing: Open access
https://doi.org/10.1002/chem.202300435

As the first known example of ring-opening cross metathesis (ROCM) of polyfluorinated strained cyclobutenes, ROCM of 3,3,4,4-tetrafluorocyclobutene with electronically rich alkenes, catalyzed by Grubbs or Hoveyda-Grubbs 2nd generation precatalysts, gave a small library of non-symmetrical isolated dienes bearing a tetrafluoroethylene spacer between the double bonds. 1-Butoxy-3,3,4,4-tetrafluorohexa-1,5-diene thus formed underwent subsequent regioselective cross metathesis (CM) with a series of styrenes, catalyzed by Hoveyda-Grubbs 2nd generation precatalyst, leading to non-symmetrically substituted dienes. 6,6-Dibutoxy-3,3,4,4-tetrafluorohex-1-ene, formed by regioselective butoxylation of 1-butoxy-3,3,4,4-tetrafluorohexa-1,5-diene, was dihydroxylated and cyclized to the corresponding 3,3,4,4-tetrafluorohexopyranose.
Permanent Link: https://hdl.handle.net/11104/0342813