Ethylenediamine, reaction with fluorinated

Aliphatic diamines (mostly 1,2-ethylenediamine) are much less studied and often give poor results in the reaction with fluorinated 1,2-bis-electrophiles possibly the only exception is diaminomaleonitrile (394), which also gives aromatic systems in these transformations. 

Acetophenone, A/-methyloxazolidine derivative, lithiation, 56, 261 Acetyl hypofluorite fluorination of uracil by, 59, 3 fluorination using, 60, 7 reaction with pyridines, 58, 280, 289 Acetylacetone, hexafluoro-, reaction with ethylenediamine, 56, 3 Acetylene cyclic dimer, trimer. tetramer, dissociation energies, 56, 343 Acetylenes, activated reactions with 3-diazo-azoles, 59, 70... 

While nonfluorinated 1,3-diketones on Cu+2 and Ni+2 matrices form N,N -ethylenebis-(aminovinylketone) chelates in their reactions with ethylenediamine, fluorinated 1,3-diketones give 2,3-dihydro-1 //-l, 4-diazepines 39 via the intermediate formation of metal chelates. 

Compounds 91 or 93 ° , 75 fluorinated p-diketones, and nitrogen derivatives 94 were employed in the preparation of fluorinated 1,4-diazepines 103-105 through the reaction with ethylenediamine (98) or its perchlorate complex (Fig. 10.39). 

Several examples demonstrating the synthesis of fluorinated 1,4-diazepines are given below. The reaction of 16 with ethylenediamine or o-phenylenediamine results in the formation of 1,4-diazepine 99 and 100, but the reaction of 24 with o-phenylenediamines 101 under similar conditions leads to the tetracyclic compounds 102 (Fig. 10.38). ... 

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