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Identifier

000414227

Title

Ανάπτυξη και εφαρμογή βιώσιμων συνθετικών τεχνολογιών του διεγερμένου οξυγόνου. Φωτοξειδώσεις συνεχούς ροής σε εκνέφωμα.

Alternative Title

Development and application of sustainable singlet oxygen based synthetic technologies. Continuous flow photooxidations in nebula.

Author

Ιωάννου, Γεώργιος Ι.

Thesis advisor

Βασιλικογιαννάκης, Γεώργιος

Reviewer

Κατερινόπουλος, Χαράλαμπος
Στρατάκης, Μανώλης
Σμόνου, Ιουλία
Περγαντής, Σπυρίδων
Μήλιος, Κωνσταντίνος
Σπύρος, Απόστολος

Abstract

In Chapter 1 of this dissertation, an introduction to the chemistry of singlet oxygen (¹Ο₂) and continuous flow photochemistry in micro- and macroreactors is presented. The advantages of continuous flow photochemistry are highlighted and compared with batch photochemistry. Additionally, some applications of the chemistry of ¹Ο₂ in continuous flow micro- and macroreactors are described. In Chapter 2 a very efficient and highly innovative continuous flow reactor NebPhotOX is presented. The “heart” of the system is a pneumatic nebulizer for undertaking large scale photooxidations. The application of this system for the onepot synthesis of a series of hydroxycyclopent-2-enones and methoxycyclopent-2-enons from simple furans, is described. In Chapter 3, a methodology for the one-pot transformation of simple furans into γ-lactams including aromatic nitrogen-bearing polycyclic systems, is described. The key step of this methodology is the intramolecular trapping of the reactive intermediate N-acyliminium ion (NAI) formed during the reaction sequence. A similar protocol was applied to the synthesis of the imidazole alkaloids glochidine and glochidicine. The outcome of the tandem reaction sequence was successfully manipulated by appropriate selection of both the photosensitizer and the solvent. Last, but not least, the synthesis of γ-lactams on a large scale using the reactor NebPhotOX is reported. In Chapter 4, studies and synthetic approaches towards the stereoselective synthesis of the natural products attenol A and attenol B are delineated. The key step of the proposed methodology is the formation of the 6,8-dioxabicyclo[3.2.1]octane system initiated by a [4+2] cycloaddition of ¹Ο₂ to appropriately substituted furan.

Language

Greek

Subject

Aerosol

Cascade reactions

Continuous flow photochemistry

Continuous flow photoreactor

Furan photooxidation

Glochidine

N-acyliminium

N-ακυλοϊμινικό ιόν

Pictet-Spengler