TY - JOUR
T1 - Preparation and Isolation of Three Isomeric C70 Isoxazolines
T2 - Strong Deshielding in the Polar Region of C70
AU - Meier, Mark S.
AU - Compton, Amy L.
AU - Shaw, Jonathan P.
AU - Selegue, John P.
AU - Guarr, Thomas F.
AU - Poplawska, Magdalena
PY - 1994/8/1
Y1 - 1994/8/1
N2 - The C70 fullerene reacts with acetonitrile oxide and with 4-methoxybenzonitrile oxide to form a mixture of three isomeric monoadducts in addition to small amounts of di- and triadducts. The three isomeric monoadducts were separated and were found to result from 1,3-dipolar addition to 6-6 ring fusions of C70 at the 1,9 position and at the 7,8 position. The 1,9 addition occurs in two different modes, while addition at the 7,8 positions results in an unseparated d,l pair of isomers. Proton NMR indicates that the fullerene moiety is strongly deshielding and that the deshielding is stronger over the poles of the fullerene than over the sides.
AB - The C70 fullerene reacts with acetonitrile oxide and with 4-methoxybenzonitrile oxide to form a mixture of three isomeric monoadducts in addition to small amounts of di- and triadducts. The three isomeric monoadducts were separated and were found to result from 1,3-dipolar addition to 6-6 ring fusions of C70 at the 1,9 position and at the 7,8 position. The 1,9 addition occurs in two different modes, while addition at the 7,8 positions results in an unseparated d,l pair of isomers. Proton NMR indicates that the fullerene moiety is strongly deshielding and that the deshielding is stronger over the poles of the fullerene than over the sides.
UR - https://www.scopus.com/pages/publications/0028493480
UR - https://www.scopus.com/inward/citedby.url?scp=0028493480&partnerID=8YFLogxK
U2 - 10.1021/ja00095a005
DO - 10.1021/ja00095a005
M3 - Article
AN - SCOPUS:0028493480
SN - 0002-7863
VL - 116
SP - 7044
EP - 7048
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 16
ER -