Related Experiment Video
Updated: Mar 26, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Synthesis of α,ω-polyfluorinated α-amino acid derivatives and δ,δ-difluoronorvaline
Dirk Ulbrich1, Constantin G Daniliuc2, Günter Haufe1
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, D-48149 Münster, Germany. haufe@uni-muenster.de and Cells-in-Motion Cluster of Excellence, Westfälische Wilhelms-Universität, Waldeyerstraße 15, D-48149 Münster, Germany.
Abstract:
Intending to synthesize ω,ω-difluoroalkyl amino acid derivatives by oxidative desulfurization-fluorination reactions of suitable arylthio-2-phthalimido butanoates and pentanoates, in addition to small amounts of the target products, mainly α,ω-polyfluorinated amino acid derivatives were formed by additional sulfur-assisted α-fluorination. This novel structural motif was verified spectroscopically as well as by X-ray analysis. A plausible mechanism of formation is suggested. Using a different approach, δ,δ-difluoronorvaline hydrochloride was synthesized with at least 36% enantiomeric excess via deoxofluorination of the corresponding aldehyde.
Related Concept Videos
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

