Reazioni di vari reagenti elettrofili con derivati amminotiazolici ad elevato potere nucleofilo

Padovan, Daniele (2013) Reazioni di vari reagenti elettrofili con derivati amminotiazolici ad elevato potere nucleofilo. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270]
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The nucleophile/electrophile combination in the aromatic substitution reaction using aminothiazole derivatives as nucleophiles has been the subject of this study. The reaction between 2,4-dipyrrolidinylthiazole and the neutral carbon electrophile 1,3,5-trinitrobenzene gave a stable Wheland-Meisenheimer (WM) complex. This represents another example, among those already found by the research group in which this work has been carried out, of stable zwitterionic σ-intermediates. When the reaction was carried out with halonitrobenzene derivatives, it produced the substitution product in position 5 of the thiazole ring. 2,4-dipyrrolidinylthiazole and arenediazonium salts gave the coupling product at the C5 of the thiazole ring together with many byproducts and the stable Wheland intermediate formed by attack of the proton on the C5 of the starting thiazole reagent. Arenediazonium salts were coupled also with 2-pyrrolidinylthiazole. In this case quantitative formation of the substitution product deriving from the attack of the electrophile on the carbon nucleophilic position of the thiazole ring was obtained. In conclusion, the results had allowed to expand the knowledge on electrophilic/nucleophilic interactions in the aromatic substitution involving thiazole heteroaromatics and provided a further example of stable Wheland-Meisenheimer intermediates.

Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
Padovan, Daniele
Relatore della tesi
Correlatore della tesi
Corso di studio
Ordinamento Cds
Parole chiave
sostituzione aromatica, derivati amminotiazolici, sali di diazonio, 1,3,5-Trinitrobenzene, meccanismi di reazione
Data di discussione della Tesi
26 Luglio 2013

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