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

doi:10.1021/jo102332e

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

J Org Chem. 2011 Apr 15;76(8):2548-57. doi: 10.1021/jo102332e. Epub 2011 Mar 10.

Authors

Irina P Romanova¹, 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

Affiliation

¹ A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, Arbuzov str., 8 Kazan 420088 Russia.

PMID: 21391680
DOI: 10.1021/jo102332e

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.