- Chemical transformations on the surface of [60]fullerene: Synthesis of [60]fullereno[1′,2′:4,5]oxazolidin-2-one
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Base-induced α-elimination from substituted 0-4-nitrophenylsulfonylhydroxamic acids has been used as a mild source of nitrenes for capture by [60]fullerene; rearrangment of the resulting [60]fullereno[1′,2′:2,3]aziridine bearing a N-ethoxycarbonyl groupin
- Banks, Malcolm R.,Cadogan,Gosney, Ian,Hodgson, Philip K. G.,Langridge-Smit, Patrick R. R.,Millar, John R. A.,Taylor, Alan T.
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- Bis-Functionalisation of C60 via Thermal Rearrangement of an Isolable Fulleroaziridine Bearing a 'Solubilising' Supermesityl Ester Moiety
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Heating of C60 with the novel azidoformate 3 bearing a highly solubilising supermesityl group affords the first example of a nitrogen-bridged fullerene 4 with a ?-homoaromatic closed 6,6-aziridine structure, which by further heating can be induced to unde
- Banks, Malcolm R.,Cadogan, J. I. G.,Gosney, Ian,Hodgson, Philip K. G.,Langridge-Smith, Patrick R. R.,Rankin, David W. H.
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- Synthesis of polyalkylphenyl prop-2-ynoates and their flash vacuum pyrolysis to polyalkylcyclohepta[b]furan-2(2H)-ones
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A new method for the smooth and highly efficient preparation of polyalkylated aryl propiolates has been developed. It is based on the formation of the corresponding aryl carbonochloridates (cf Scheme 1 and Table 1) that react with sodium (or lithium) propiolate in THF at 25-65°, with intermediate generation of the mixed anhydrides of the arylcarbonic acids and prop-2-ynoic acid, which then decompose almost quantitatively into CO2 and the aryl propiolates (cf. Scheme 11). This procedure is superior to the transformation of propynoic acid into its difficult-to-handle acid chloride, which is then reacted with sodium (or lithium) arenolates. A number of the polyalkylated aryl propiolates were subjected to flash vacuum pyrolysis (FVP) at 600-650°and 10-2 Torr which led to the formation of the corresponding cyclohepta[b]furan-2(2H)-ones in average yields of 25-45% (cf. Scheme 14). It has further been found in pilot experiments that the polyalkylated cyclohepta[b]furan-2(2H)-ones react with 1-(pyrrolidin-1-yl)cyclohexene in toluene at 120-130°to yield the corresponding 1,2,3,4- tetrahydrobenz[a]azulenes, which become, with the growing number of Me groups at the seven-membered ring, more and more sensitive to oxidative destruction by air (cf. Scheme 15).
- Nagel, Matthias,Hansen, Hans-Juergen
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p. 1022 - 1048
(2007/10/03)
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- Synthesis and Photolysis of N-(Phenoxycarbonyloxy)-2-thiopyridone Derivatives. A New Unimolecular Route to Quantitative Generation of Phenoxyl Radicals
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N-(Phenoxycarbonyloxy)-2-thiopyridone derivatives were prepared by the reaction of lithium phenoxides with phosgene followed by the reaction with 2-mercaptopyridine N-oxide and photolyzed to give quantitative yield of phenoxyl radicals.
- Togo, Yoshifumi,Nakamura, Nobuo,Iwamura, Hiizu
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p. 1201 - 1204
(2007/10/02)
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