Synthesis of fluorinated telechelic diols based on 3,3,3-trifluoropropene as precursors of well-defined fluoropolymers

Georgi K Kostov; Gérald Lopez; Stephan M Brandstadter; Bradley E Edwards; Bruno Améduri

doi:10.1021/ol501466c

Synthesis of fluorinated telechelic diols based on 3,3,3-trifluoropropene as precursors of well-defined fluoropolymers

Org Lett. 2014 Jul 3;16(13):3516-9. doi: 10.1021/ol501466c. Epub 2014 Jun 24.

Authors

Georgi K Kostov¹, Gérald Lopez, Stephan M Brandstadter, Bradley E Edwards, Bruno Améduri

Affiliation

¹ Institut Charles Gerhardt de Montpellier (ICGM) - UMR 5253, Ingénierie et Architectures Macromoléculaires (IAM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM) , 8 Rue de l'Ecole Normale, 34296 Montpellier, France.

PMID: 24960523
DOI: 10.1021/ol501466c

Abstract

Original fluorinated α,ω-diols containing 3,3,3-trifluoropropene (TFP) units were synthesized. The first step dealt with the radical telomerization of TFP with 1,6-diiodoperfluorohexane. Isolated I(TFP)RF(TFP)I diadduct was subsequently reacted with ethylene, and then a two-step hydrolysis gave rise to α,ω-diols in 25% overall yield. The other strategies dealing with the radical addition of I(TFP)RF(TFP)I onto allyl alcohol or allyl acetate led to α,ω-diols in 13% overall yield. These diols display satisfactory thermal stabilities and low Tg (ca. -60 °C).