Organic Chemistry Portal

Abstracts

Search:

Halo- and Azidodediazoniation of Arenediazonium Tetrafluoroborates with Trimethylsilyl Halides and Trimethylsilyl Azide and Sandmeyer-Type Bromodediazoniation with Cu(I)Br in [BMIM][PF6] Ionic Liquid

Abigail Hubbard, Takao Okazaki and Kenneth K. Laali*

*Department of Chemistry, Kent State University, Kent, Ohio 44242, Email: klaalikent.edu

A. Hubbard, T. Okazaki, K. K. Laali, J. Org. Chem., 2008, 73, 316-319.

DOI: 10.1021/jo701937e (free Supporting Information)


Abstract

Reaction of [ArN2][BF4] salts immobilized in [BMIM][PF6] ionic liquid (IL) with TMSI and TMSN3 represents an efficient method for the preparation of iodo- and azido-derivatives via dediazoniation. Using TMSBr, competing fluorodediazoniation (ArF formation) and hydrodediazoniation (ArH formation) were observed depending on the substituents on the benzenediazonium cation.

see article for more examples



Fluorodediazonization in ionic liquid solvents: new life for the Balz-Schiemann reaction

K. K. Laali, V. J. Gettwert, J. Fluorine Chem., 2001, 107, 31-34.


Key Words

Sandmeyer Reaction, Aryl Azides, Aryl Iodides, Ionic Liquids


ID: J42-Y2008-0220