TY - JOUR
T1 - Photocycloaddition of cyclic 1,3-diones to C60
AU - Jensen, Anton W.
AU - Khong, Anthony
AU - Saunders, Martin
AU - Wilson, Steven R.
AU - Schuster, David I.
PY - 1997/8/6
Y1 - 1997/8/6
N2 - Irradiation of cyclic 1,3-diones (1a and 2a) with C60 in benzene leads to formation of two fused furanylfullerenes, one achiral (3) and the other chiral (4), as opposed to the expected De Mayo cyclooctane-1,3-dione addition product. The same products are obtained when 1,3-diones are replaced with trimethylsilyl-protected diones (1b and 2b). The adduct structures were characterized by MS CESI and MALDI), IR, UV, 1H NMR, 13C NMR, and 3He NMR spectroscopy. These fullerene adducts presumably are formed after initial [2 + 2] photocycloaddition, followed by either intermolecular oxidation of the cyclobutyl intermediates (5-8) by 1O2 to form 3 or intramolecular oxidation of the appended group by the triplet fullerene moiety of 5-8 to form 4.
AB - Irradiation of cyclic 1,3-diones (1a and 2a) with C60 in benzene leads to formation of two fused furanylfullerenes, one achiral (3) and the other chiral (4), as opposed to the expected De Mayo cyclooctane-1,3-dione addition product. The same products are obtained when 1,3-diones are replaced with trimethylsilyl-protected diones (1b and 2b). The adduct structures were characterized by MS CESI and MALDI), IR, UV, 1H NMR, 13C NMR, and 3He NMR spectroscopy. These fullerene adducts presumably are formed after initial [2 + 2] photocycloaddition, followed by either intermolecular oxidation of the cyclobutyl intermediates (5-8) by 1O2 to form 3 or intramolecular oxidation of the appended group by the triplet fullerene moiety of 5-8 to form 4.
UR - http://www.scopus.com/inward/record.url?scp=0030814690&partnerID=8YFLogxK
U2 - 10.1021/ja962509t
DO - 10.1021/ja962509t
M3 - Article
AN - SCOPUS:0030814690
VL - 119
SP - 7303
EP - 7307
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 31
ER -