Dissertation > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Elements in organic compounds

Synthesis of Osmafuran, Osmanaphthalene and Osmapyridine by [4+1], [5+1] and [4+2] Cyclization Methods

Author LiuBin
Tutor XiaHaiPing
School Xiamen University
Course Polymer Chemistry and Physics
Keywords Metal heteroaromatic compounds The activation of C-H [ 42 ] cycloaddition reaction Metal naphthalene Metal pyridine
CLC O627
Type PhD thesis
Year 2009
Downloads 99
Quotes 1
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Metal heteroaromatic chemistry is a new field of research produced by cross-cutting between the aromatic chemical and metal organic chemical. In recent years, increasingly attracted the attention of scientists metal heteroaromatic compounds have potential special optical, electrical and magnetic properties. Such compounds not only has the characteristics of the aromatic compound, such as cyclic, conjugated, a planar structure, low-field chemical shift, but also due to the presence of a metal-carbon multiple bond (MC), and further comprising the reaction of the organometallic compound. Known species: metal benzene, metal benzyne, metal pyridine, metal topiramate feeding onium the thia-metal benzene metal pyrrole, metal furan, metal thiophene, metal naphthalene, metal naphthalene propargyl, metal benzo furan. Wherein the metal heteroaryl fused aromatic ring of (metal naphthyl, metal naphthyl propargyl, etc.), and other hetero atom-containing metal heteroaromatic compound (metal, pyridine, etc.) less. This paper studies a the the metal reagents OsCl 2 (the PPh 3 ) 3 and alkynol ligand reaction of HC ≡ CCH (OH) Ph: [41] cyclization synthesized osmium furan compounds; synthesized by [51] cyclization of the first case of metal naphthalene dimer, and the second case of metal naphthalene-acetylene; first discovered metal hybrid 1,3 - butadiene and nitrile [4 2] cycloaddition reaction, obtained first after pyridine and its derivatives of the transition metal metal pyridine salt. The paper is divided into the following five parts: The first chapter is the introduction, the metal heteroaromatic compounds Research. Can be seen, the current research in the area of ??focus is still on the synthesis of novel metal hetero aromatic compound, wherein the metal benzene higher homologues (metal naphthyl, metal naphthyl alkynyl, etc.), and part of main group-containing hetero atoms (nitrogen, oxygen heteroaromatic compound (metal pyridine), sulfur, etc.) of the metal is relatively small. Based on the status quo of this study, combined with the characteristics of the laboratory studies, the use of [41] the synthesis of metal furan, [51] synthesis of metal naphthalene and [42] cycloaddition synthesis of metal pyridine ideas. The second chapter studies the the metal reagent OsCl 2 (PPh 3 ) 3 alkynol ligand reaction of HC ≡ CCH (OH) Ph hydroxy intramolecular ligand annular osmium vinyl compound 2-1 (Scheme 1). The reaction of the compound (Scheme 2), and found that the effect of the heating or alkali 2-1 can be converted to osmium furan compounds 2-2 and 2-3. This can be seen as a [41] cyclization method in the aspects of the synthesis of metal furan. 2-1 CO and DPPB (Ph 2 P (CH 2 ) 4 PPh 2 ) reaction were obtained osmium vinyl compound 2-4 and 2-5. Chapter III study the metalliferous hydrogen osmium carbyne the compounds 3-2 Synthesis and Reactivity (Scheme3), metal hydrogen migration reaction of carbon atoms and phenyl CH activation carbyne selective synthesis the first case of metal naphthalene dimers 3-3 and the second case of metal naphthalene-acetylene 3-4. And to achieve the conversion of the metal of naphthalene to metal naphthyl alkynyl, which can also be seen as the first metal benzene conversion to the metal benzyne, provides a potential application of synthesis method for the synthesis of metal benzyne. ,3-2 can also occur with H 2 O [41] cyclization reaction of hydroxyl molecule ligand the cyclic osmium vinyl compounds 3-5 (Scheme 4). The fourth chapter studies the reaction of compounds 3-2 with acetonitrile (Scheme 5). Found that they can occur in form [42] cycloaddition reaction after the first transition series metal pyridine 4-2, and their derivatives metal pyridinium salts 4-1. Compound 4-1 and 4-2 having a paramagnetic, not found in other metals heteroaromatic compound study reported. Compound 4-1 may also occur with H 2 O nucleophilic addition reactions get nitrogen the osmium heterocyclic compounds of the hexadiene 4-3 (Scheme 6). Similar reaction in the metal heteroaromatic chemistry only two cases (same story). The fifth chapter summarizes the thesis innovative, and the prospect of future research work.

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