Iron, tricarbonyl acylation electrophilic reactions

Azepines do not undergo electrophilic substitution reactions and introduction of substituents at the 3-or 4-position is a difficult problem. Acylation at C-3 can be achieved via the iron tricarbonyl complex as shown in Scheme 22.42 The N-ethoxycarbonyl group of the acylated product can be removed with methoxide methanol and the resulting 1H compound can then be methylated. 

Diels-Alder reactions, 4, 842 flash vapour phase pyrolysis, 4, 846 reactions with 6-dimethylaminofuKenov, 4, 844 reactions with JV,n-diphenylnitrone, 4, 841 reactions with mesitonitrile oxide, 4, 841 structure, 4, 715, 725 synthesis, 4, 725, 767-769, 930 theoretical methods, 4, 3 tricarbonyl iron complexes, 4, 847 dipole moments, 4, 716 n-directing effect, 4, 44 2,5-disubstituted synthesis, 4, 116-117 from l,3-dithiolylium-4-olates, 6, 826 electrocyclization, 4, 748-750 electron bombardment, 4, 739 electronic deformation, 4, 722-723 electronic structure, 4, 715 electrophilic substitution, 4, 43, 44, 717-719, 751 directing effects, 4, 752-753 fluorescence spectra, 4, 735-736 fluorinated derivatives, 4, 679 H NMR, 4, 731 Friedel-Crafts acylation, 4, 777 with fused six-membered heterocyclic rings, 4, 973-1036 fused small rings structure, 4, 720-721 gas phase UV spectrum, 4, 734 H NMR, 4, 7, 728-731, 939 solvent effects, 4, 730 substituent constants, 4, 731 halo... 

The most used reaction with respect to electrophilic substitution at (diene)iron complexes is the acylation. (Dienone)iron complexes are obtained by reaction of acyclic tricarbonyl(Ti -l,3-diene)iron complexes with carboxylic acid chlorides in the presence of aluminum trichloride in high yields (Scheme 4-11 i).P65-271]... 

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