New reaction of fullerenes. [2 + 2] photocycloaddition of enones

Journal Article · Wed Sep 08 00:00:00 EDT 1993 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00071a088· OSTI ID:5147227

Wilson, S R; Kaprinidis, N; Wu, Y; Schuster, D L ^[1]

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1. New York Univ., NY (United States)

We now report functionalization of C[sub 60] by [2 + 2] photocycloaddition of cyclic enones, allowing the simple preparation of a large new class of C[sub 60] derivatives. This is another application of a classic photochemical reaction which is widely used synthetically. The mechanistic features also are of considerable interest. We have shown (a) that the new technique of electrospray ionization mass spectrometry (ESI-MS) is a uniquely suitable tool for studying the reactions of fullerenes, (b) that a variety of functionally substituted derivatives of C[sub 60] can be prepared by [2 + 2] photocycloaddition to cyclic enones, and (c) that these adducts arise by the stepwise addition of enone triplets to the fullerenes. 29 refs., 1 fig.

• OSTI ID: 5147227
• Journal Information: Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 115:18; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400102 -- Chemical & Spectral Procedures
400201* -- Chemical & Physicochemical Properties
ADDUCTS
CARBON
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DERIVATIZATION
ELEMENTS
FULLERENES
IONIZATION
KETONES
KINETICS
MASS SPECTROSCOPY
NONMETALS
ORGANIC COMPOUNDS
PHOTOCHEMICAL REACTIONS
REACTION KINETICS
SPECTROSCOPY
SYNTHESIS