Abstract
The cyclopentadienyl type hexa-adduct C(60)(OOtBu)(6) 1 is readily converted into 2H-pyran containing fullerene derivative C(60)(O)(OOH)(OOtBu)(5) 2 in the presence of NaHCO(3) and hydroquinone. In the process, O-O bond of the tert-butylperoxo group on the central pentagon is cleaved, and the fullerene-bound oxygen radical inserts into a 5,6-junction to form the 2H-pyran moiety. Further reactions of 2 led to open-cage fullerenes with a nine-membered orifice and also both 3,4-dihydro-2H-pyran and 3,6-dihydro-2H-pyran containing fullerene derivatives. Mechanisms are proposed involving intramolecular S(N)2' and aza-Michael addition and ketal formation processes.
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