Romano, Angela
(2017)
Synthesis and characterization of new chiral molecules: 1,2,5,8-dithiadiazecine-6,7(5H,8H)-dione derivatives.
[Laurea magistrale], Università di Bologna, Corso di Studio in
Chimica industriale [LM-DM270], Documento ad accesso riservato.
Documenti full-text disponibili:
![[img]](http://amslaurea.unibo.it/style/images/fileicons/application_pdf.png) |
Documento PDF (Thesis)
Full-text non accessibile fino al 31 Dicembre 2046.
Disponibile con Licenza: Salvo eventuali più ampie autorizzazioni dell'autore, la tesi può essere liberamente consultata e può essere effettuato il salvataggio e la stampa di una copia per fini strettamente personali di studio, di ricerca e di insegnamento, con espresso divieto di qualunque utilizzo direttamente o indirettamente commerciale. Ogni altro diritto sul materiale è riservato
Download (2MB)
| Contatta l'autore
|
Abstract
The synthesis of ten-membered rings is not obvious. During this project, a new synthetic pathway was developed, which involves reaction of a benzothiazolium salt with a base and subsequent oxidation to air. The resulting ten-membered ring (1,2,5,8-dithiadiazecine-6,7(5H,8H)-dione 1) is inherently chiral because of constrained rotation about its interdependent stereogenic axes, and two enantiomers were detected and resolved by HPLC. The chiral properties of these enantiomers were studied by polarimetry, ECD spectrometry and X-ray and absolute configuration was assigned by DFT calculations. It was interesting to observe how chiral properties could change by oxidizing one sulphur atom, therefore 5,8-dimethyldibenzo[1,2,5,8]-dithiadiazecine-6,7(5H,8H)-dione-1-oxide 7 and 5,8-dimethyldibenzo[1,2,5,8]-dithiadiazecine-6,7(5H,8H)-dione-1,1-dioxide 8 were synthetized and characterized in the same way of compound 1.
Abstract
The synthesis of ten-membered rings is not obvious. During this project, a new synthetic pathway was developed, which involves reaction of a benzothiazolium salt with a base and subsequent oxidation to air. The resulting ten-membered ring (1,2,5,8-dithiadiazecine-6,7(5H,8H)-dione 1) is inherently chiral because of constrained rotation about its interdependent stereogenic axes, and two enantiomers were detected and resolved by HPLC. The chiral properties of these enantiomers were studied by polarimetry, ECD spectrometry and X-ray and absolute configuration was assigned by DFT calculations. It was interesting to observe how chiral properties could change by oxidizing one sulphur atom, therefore 5,8-dimethyldibenzo[1,2,5,8]-dithiadiazecine-6,7(5H,8H)-dione-1-oxide 7 and 5,8-dimethyldibenzo[1,2,5,8]-dithiadiazecine-6,7(5H,8H)-dione-1,1-dioxide 8 were synthetized and characterized in the same way of compound 1.
Tipologia del documento
Tesi di laurea
(Laurea magistrale)
Autore della tesi
Romano, Angela
Relatore della tesi
Correlatore della tesi
Scuola
Corso di studio
Ordinamento Cds
DM270
Parole chiave
inherent chirality ten-membered ring enantiomerization energy barrier absolute configuration
Data di discussione della Tesi
20 Marzo 2017
URI
Altri metadati
Tipologia del documento
Tesi di laurea
(NON SPECIFICATO)
Autore della tesi
Romano, Angela
Relatore della tesi
Correlatore della tesi
Scuola
Corso di studio
Ordinamento Cds
DM270
Parole chiave
inherent chirality ten-membered ring enantiomerization energy barrier absolute configuration
Data di discussione della Tesi
20 Marzo 2017
URI
Gestione del documento: