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Synlett 2010(15): 2363-2364  
DOI: 10.1055/s-0030-1258051
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© Georg Thieme Verlag Stuttgart ˙ New York

Hexafluoroacetone: An Appealing Key Player in Organic Chemistry

Kirandeep Kaur*
Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India
e-Mail: kirandeepkahlon08@gmail.com;
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Publication History

Publication Date:
30 August 2010 (online)

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Introduction

Hexafluoroacetone (HFA, CAS: 684-16-2), a colorless, non-flammable, musty odour gas with a boiling point of -28 ˚C, is an efficient site-selective reagent in organic synthesis. [¹] It is also found in liquid form and is used in the synthesis of solvents, adhesives and pharmaceutical products. It is a highly reactive electrophile. It reacts with activated aromatic compounds and can be condensed with olefins, dienes, ketenes, and acetylenes. HFA is a very important reagent in the solid-phase synthesis and modification of peptides, glyco- and depsipeptides. [²] In contrast to the conventional protecting groups for peptide synthesis, it is a bidentate reagent and protects simultaneously the carboxyl group and the α-functionality. Hexafluoroacetone is widely used in the synthesis of monomers that are used to prepare speciality polymers. [³] In analytical studies, HFA can be used as a reagent in ¹9F NMR spectroscopy of compounds comprising active hydrogens. [4]