Study On The Synthesis And Properties Of Diaryl Iodonium Salts

Diaryliodonium salts represent an important class of aromatic iodoine(III)derivatives. They are used mostly as arylating reagent for a large variety of organicand inorganic nucleophiles in organic synthesis. Some of them display a biologicalactivity or photochemical properties, hence they are widely used as activephotoinitiators of cationic polymerization. Recently, they have been shown to beuseful precursor for the synthesis of radiopharmaceuticals for positron emissiontomography(PET).According to the reported synthetic route, we synthesized two diaryliodoniumsalts, 4,4'-dimethyl diphenyliodonium hexafluorophosphates and 4-methyl-4'-iso-butyl diphenyliodonium hexafluorophosphates, which can be used as cationicphotoinitiators. Sodium perborate tetrahydrate was used for the first time as theoxidant in the synthesis of the latter compound. The new procedure was easy, cheap,safeandeffective.In this thesis, the synthesis routes of unsymmetric diaryliodonium salts wereoptimized and a series of new unsymmetric diaryliodonium trifluoroacetatescontaining electron-donating groups (MeO, Me) were synthesized. In addition, weprovided a new procedure to synthesize aryl azides by reaction of diaryliodoniumtrifluoroacetates and sodium azide in a two-phase water-chlorom system. Thestructuresofallcompoundswereconfirmedby1H-NMRand13C-NMRspectra.In addition, the influence of the electron-donating group on the synthesis ofdiaryliodoniumsaltsandtheattackpositionoftheazideanionwerealsostudied.