Affiliation:
1. Department or Organic Chemistry University of Chemistry and Technology, Prague Technická 5 166 28 Prague 6 Czech Republic
2. Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo náměstí 542/2 160 00 Praha 6, Prague Czech Republic
3. Department of Solid State Chemistry University of Chemistry and Technology, Prague Technická 5 166 28 Prague 6 Czech Republic
Abstract
AbstractAs 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.
Funder
Grantová Agentura České Republiky
Subject
General Chemistry,Catalysis,Organic Chemistry