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Identifier

000315843

Title

Χημεία του διεγερμένου οξυγόνου και των RTADs με πυρρολικούς και φουρανικούς δακτυλίους

Alternative Title

Chemistry of excited oxygen and RTADs with pyrrole and furan rings

Author

Αλμπέρτη, Μαρία-Ιωάννα Νικολάου

Thesis advisor

Ορφανόπουλος, Μιχαήλ

Abstract

This dissertation includes the study of the singlet oxygen and RTAD reactions of substituted pyrroles and furans. In the first chapter, the photooxidations of N-hydroxyalkyl substituted pyrroles were investigated. Eleven new products were isolated and characterized using NMR spectroscopy. In most cases the bicyclic lactams were the minor products observed, in contrast to previously reported studies. Furthermore, the photooxidation of 1-(2-hydroxyethyl)-2,5-dimethylpyrrole yielded three unexpected products, that are reported for the first time. In the second chapter, the RTAD reactions of substituted pyrroles and furans were investigated. Twenty-one new products were isolated and characterized using NMR spectroscopy. Particularly, substituted pyrroles reacted with PTAD to give the corresponding adducts. 2,5-Dimethylfuran reacted in CDCl3 with PTAD to give the [4+2] adducts. In the other hand, furan and 2-methylfuran reacted in CDCl3 with PTAD and a complex mixture of unidentified polar or/and polymeric materials were formed. Furthermore, when substituted and non substituted furans reacted in MeOH with PTAD, the solvent-trapped adducts were formed. These products were mainly derived from the corresponding 1,4-dipolar intermediates.

Language

Greek

Subject

Furan

Photooxidation

Pyrrole

RTAD

Singlet oxygen

Διεγερμένο μοριακό οξυγόνο απλής κατάστασης

Πυρρόλιο

Τριαζολινοδιόνη

Φωτοοξείδωση