Reaktionen von Diaminen mit Fulleren C60

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Abstract
Reactions of Diamines with Fullerene C60Reactions of 1,2‐ and 1,3‐diamines 2a‐i, including diamines containing primary amino groups, with C60 (1) in toluene are described, leading to mono‐ and bisadducts 3–16. In this way fullerene derivatives carrying NH as a nucleophilic functional group have been synthesized. Yields and ratios of mono‐ and bisadducts formed depend on reaction conditions and on the structure of the diamine. The scope of this reaction leading to defined mono‐ and bisadducts in appreciable yields has been investigated. Mono‐ and bisadducts formed can be separated by column chromatography on SiO2. Mass and NMR spectra reveal that the isolated basic fullerene derivatives are dehydro adducts. NMR spectra show that the monoadducts have a symmetrical structure. In all cases investigated the addition forming the mono‐ and bisadducts of 1 occurs across a 6–6 bond. Likewise analogous additions take place with C70. Remarkably, tertiary diamines such as 2p and q react with 1 forming the monoadduct 8 in small yields by loss of an alkyl group. Proposed structures of some regioisomeric bisadducts are discussed.