Malonyl fluoride

Malonyl fluoride forms the diacyl cation (24), which is in equilibrium with the donor-acceptor complex (23). The higher homologs of the dications are quite stable. ... 

Chromium carbene complexes. phloroglucinols Malonyl dichloride. phthalides Thallium(III) trifluoroacetate. pinacols Samarium(II) iodide. Tetra-w-butylammonium fluoride. 

The starting phenylenediamine (12) was prepared by reaction of a 2-fluoronitro benzene (9) with an aniline (10) in the presence of potassium fluoride and subsequent reduction of the nitro derivative (11). The resulting amine (12) was generally alkylated with an alkyl bromide in the presence of sodium iodide to obtain the intermediate (13). However, when bulky groups had to be introduced, the intermediate (13 ) was conveniently obtained by reductive amination of either aldehydes or ketones. Condensation of (13) with (phenylhydrazono)malonyl dichloride followed by reduction with zinc and acetic acid led to the 3-amino substituted benzodiazepines (15). 

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