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Identifier

000315844

Title

Νέες παραγοντοποιήσεις και μηχανιστικές μελέτες σε αντιδράσεις του φουλερενίου C60 και των ετεροφουλερενίων (C59N)2 και C59HN

Alternative Title

Functionalization and mechanistic studies on the reactions of fullerene C60 and heterofullerenes (C59N)2 and C59HN

Author

Βουγιουκαλάκης, Γεώργιος Χ.

Thesis advisor

Ορφανόπουλος, Μιχαήλ

Abstract

Τhe self-photooxygenation of C₆₀-allyl substituted cis alkenes ocurrs by the preferential abstraction of an allylic hydrogen next to the fullerene group. The non-bonding steric interactions are mainly responsible for the observed regioselectivity. The hydrogen atom linked to the fullerene frame is unreactive under the photoogygenation conditions. An efficient reaction between the azafullerene dimer, (C₅₉ N)₂ and arylalkanes led to the formation of six new azafullerene monoadducts. Furthermore, the reaction between aza[60]fullerene radical and the suitable deuterium labelled arylalkanes has been mechanistically studied. The measured primary and secondary kinetic isotope effects provide strong evidence for a stepwise mechanism, in which the hydrogen atom abstraction occurs in the first, rate-determining step of the reaction, followed by a second, faster, coupling of the two radicals.

Language

Greek

Subject

arylalkanes

free radicals

fullerene C60

kinetic isotope effects

photooxidation

άρυλοαλκάνια

ελεύθερες ρίζες

κινητικά ισοτοπικά φαινόμενα

φουλερένιο C60