Preparation and isolation of three isomeric C[sub 70] isoxazolines. Strong deshielding in the polar region of C[sub 70]

The C[sub 70] 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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1994-08, Vol.116:16
Main Authors: Meier, M.S., Poplawska, M., Compton, A.L., Shaw, J.P., Selegue, J.P., Guarr, T.F.
Format: Article
Language:English
Subjects:
400102 - Chemical & Spectral Procedures
400201 - Chemical & Physicochemical Properties
400400 - Electrochemistry
ADDUCTS
CARBON
CHEMICAL REACTIONS
CHEMISTRY
ELECTROCHEMISTRY
ELEMENTS
FULLERENES
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
ISOMERS
MAGNETIC RESONANCE
NONMETALS
NUCLEAR MAGNETIC RESONANCE
RESONANCE
VOLTAMETRY
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Summary:The C[sub 70] 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 C[sub 70] 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. 74 refs., 5 figs.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00095a005