The Synthesis Of Several Fluorinated Reagents

This thesis focuses on the synthesis of the dialkylaminosulfur trifluoride and the analogues of N-fluorobenzenesulfonimide (NFSI).The synthetic process of Diethylaminosulfur trifluoride (DAST) and Bis(2-methoxyethyl)aminesulfur trifluoride (Deoxofluor) were investigated. Based on the DAST synthetic patents and papers, a novel process was developed. Under solvent-free condition, N-(Trimethylsilyl)diethylamine reacted with SF4 at low temperature, the clear diethylaminosulfur trifluoride (Purity>90%) was obtained without hazardous vacuum distillation. The synthesis of bis(2-methoxyethyl)amine was undergone by the reaction of ammonia and 2-methoxyethyl chloride, the yield is 48%. In the presence of N-methylpyrrolidine bis(2-methoxyethyl)amine reacted with SF4 in petroleum ether, The petroleum ether solution of bis(2-methoxyethyl)aminesulfur trifluoride was afforded in 75% yield with more than 90% 19F NMR purity.This paper also studied the synthetic processes of NFSI analogues. At-30-15℃in the mixture of MeCN and little water the fluorination of di(benzenesulfonyl)amine sodium salts was carried out with 10% and 20% F2/N2 mixture, NFSI analogues with p-substitutents (-t-Bu,-F,-Cl,-Br,-CH3,-CF3,-OCF3,-OMe) were synthesized in 21%-88% yields. This method with high yield and spread use was not reported in the literature.