2024-03-28T20:25:43Zhttps://www.tdx.cat/oai/requestoai:www.tdx.cat:10803/3284392017-09-19T07:32:54Zcom_10803_253col_10803_283
nam a 5i 4500
Catàlisi de metalls de transició
Transition metal catalysis
Catalizadores metálicos de transición
Cycloaddition
Cicloaddició
Cicloaddición
Allenes
Al·lens
Alenos
Rhodium
Rodio
Rodi
[2+2+2] cycloaddition reactions involving allenes catalysed by rhodium
[Girona] :
Universitat de Girona,
2015
Accés lliure
http://hdl.handle.net/10803/328439
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Haraburda, Ewelina,
autor
1 recurs en línia (299 pàgines)
Tesi
Doctorat
Universitat de Girona. Departament de Química
2015
Universitat de Girona. Departament de Química
Tesis i dissertacions electròniques
Pla i Quintana, Anna,
supervisor acadèmic
Roglans i Ribas, Anna,
supervisor acadèmic
TDX
The development of new chemical processes for the formation of carbon-carbon bonds is an important topic in organic chemistry. In particular, the transition metal catalysed [2+2+2] cycloaddition reaction is a highly efficient synthetic tool that allows six-membered polysubstituted carbo- and heterocyclic derivatives to be obtained in an atom economy process. Allenes are versatile substrates for cycloaddition reactions that provide a good reactivity profile together with the ability to increase the stereochemical complexity of the cycloadducts obtained. This doctoral thesis, divided into seven different chapters, is based on the methodological study of the rhodium(I)-catalysed [2+2+2] cycloaddition reaction involving allenes. Chapter 1 contains a general introduction to the structural and reactivity particularities of allenes and to the [2+2+2] cycloaddition reactions, making reference to the main examples found in the literature. Chapter 2 sets out the general objectives of the thesis. In Chapters 3 and 4 the reactivity of linear chiral and non-chiral allene-ene/yne-allene substrates in totally intramolecular rhodium-catalysed [2+2+2] cycloaddition is evaluated. In Chapter 5, a dehydrogenative [2+2+2] cycloaddition of cyano-yne-allene substrates is developed which allows for the synthesis of the 2,6-naphthyridines core found in biologically relevant products. Chapter 6 draws general conclusions from the results of these studies. Finally, Chapter 7 contains the experimental procedure and the characterization data for the compounds synthesised in this thesis.
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