title: 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-α-, -β-, and -δ-amino acids, as well as peptides with back-bond-bound fluorine. The strong influence on β-peptide folding by fluoro-substituents in the α-position of β-amino-acid residues is discussed in terms of the α-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.
authors.affiliation: Eidgenössische Technische Hochschule Zürich, Departement für Chemie und Angewandte, Biowissenschaften (D-CHAB), Laboratorium für Organische Chemie, HCI H331, Vladimir-Prelog-Weg 3, CH-8093 Zürich, Switzerland. Seebach@org.chem.ethz.ch.
authors.forename: Dieter
authors.initials: D
authors.lastname: Seebach
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D009930:Organic Chemicals; D010455:Peptides; D005461:Fluorine