Journal of Organic Chemistry 2011-04-15

Deoxygenation of some α-dicarbonyl compounds by tris(diethylamino)phosphine in the presence of fullerene C60.

Irina P Romanova, Andrey V Bogdanov, Vladimir F Mironov, Gulnara R Shaikhutdinova, Olga A Larionova, Shamil K Latypov, Alsu A Balandina, Dmitry G Yakhvarov, Aidar T Gubaidullin, Alina F Saifina, Oleg G Sinyashin

Index: J. Org. Chem. 76(8) , 2548-57, (2011)

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Abstract

The reactions of such cyclic α-diketones as acenaphthenequinone, aceanthrenequinone, and N-alkylisatins, with hexaethyltriaminophosphine in the presence of the fullerene C(60), lead to the formation of methanofullerene derivatives under mild conditions. This process proceeds via deoxygenation of the dicarbonyl compound by the P(III) derivative and is likely to involve the intermediate formation of α-ketocarbenes. The structure of some methanofullerenes has been confirmed by NMR and XRD. The electrochemical behavior of the methanofullerenes was also investigated.