Joy and Flustration with Organofluorine Compounds – A Fluorous Autobiography

Abstract

An overview is given about our work on fluoro-organic compounds, published or described in PhD theses between 1977 and 2013. After a discussion of structural F-effects and F-tagging applications the material is ordered by the various areas of our research, in which we have used and/or prepared F-derivatives: Li- and Ti-organic compounds and reagents, polylithiated hydroxy-esters and nitroalkanes, the enantiopure trifluoro-lactic, -Roche, and -3-hydroxy-butanoic acids as toolbox for the preparation of numerous F3C-substituted compounds, including natural products and dendrimers, and fluoro-?-, -?-, and -?-amino acids, as well as peptides with back-bond-bound fluorine. The strong influence on ?-peptide folding by fluoro-substituents in the ?-position of ?-amino-acid residues is discussed in terms of the ?-fluoro-amide conformational effect. Finally, some cases of totally unexpected effects on reactivity and structure exerted by fluoro-substitution are presented and taken as examples for our use of the terms flustrate and flustration in connection with organo-fluorine chemistry.

Keywords

• Cf3-substituted dendrimers
• Enantiopure aliphatic cf3-derivatives
• F-effects on peptide folding
• F-labelling and tagging
• Fluoro-organic compounds