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Study On The Synthesis And Catalytic Friedel-Crafts-type Reactions Of Substituted Indenyl Rhenium Carbonyl Complexes

Posted on:2017-03-19Degree:MasterType:Thesis
Country:ChinaCandidate:X L ZhangFull Text:PDF
GTID:2271330482980099Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Indene and its derivatives have the characteristics of a variety of coordination modes and the transition metal complexes containing indenyl have higher reactivity and catalytic performance than the transition metal containing cyclopentadienyl complexes. Thus it can be seen, intensive study of these complexes is of great significance, which will not only enrich and develop the metal organic chemistry theory, also help for the new model of the highly active and selective catalyst and reaction, so it has potential application prospects. This paper studied the synthesis of substituted indenyl rhenium carbonyl complexes, separation and identification of their structures, investigated the substituent effect of indenyl ring; the catalytic reactivity of Friedel-Crafts alkylation and acylation, optimized the catalyst system and reaction conditions and explored the possible mechanism of Friedel-Crafts reaction. The main research contents are as follows.(1) In this thesis, substituted indenyl ligands [C9H7R] [R= nBu(1), tBu(2), CH(CH2)4(3), Ph(4), Bz(5), 4-CH3OPh(6), 4-Cl Ph(7) were synthesized. Reactions of the seven ligands with Re2(CO)10 in refluxing decalin gave the corresponding complexes [(η5-C9H6R)Re(CO)3] [R= nBu(8), tBu(9), CH(CH2)4(10), Ph(11), Bz(12), 4-CH3OPh(13), 4-Cl Ph(14). The crystal structures of 9, 10, 12 and 13 were determined by X-ray diffraction. These four crystals have similar molecular structure, belonging to the mononuclear carbonyl complex. In each of these molecules the metal Re is η5-coordinated to the five-membered ring of indenyl group.(2) The Friedel-Crafts reactions of different aromatic compounds with various alkylation and acylation reagents catalyzed by complexes 8~14 were studied respectively. The results indicated that all the substituted indenyl rhenium carbonyl complexes have obvious catalytic activity. Compared with the traditional catalysts, the metal carbonyl complexes have obvious advantages, for example: less dosage, mild reaction condition, simple post-processing, close to the advantages of green chemistry and so on.(3) All unknown complexes were characterized by 1H NMR, 13 C NMR, IR spectra and elemental analysis.
Keywords/Search Tags:substituted indenyl, rhenium carbonyl complex, catalysis, Friedel-Crafts alkylation reaction, Friedel-Crafts acylation reaction
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