Aziridino[2′,3′ : 1,2][60]fullerene

Banks, Malcolm R.; Cadogan, J. I. G.; Gosney, Ian; Hodgson, P. K. G.; Langridge‐Smith, Patrick R. R.; Millar, J. R.; Taylor, Anne

doi:10.1039/c39950000885

Cited by 56 publications

(26 citation statements)

References 6 publications

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“…Purification by flash chromatography with 25% ethyl acetate/n-hexane provided the title compound as a white-yellow solid (0.881 g, 46%), mp 86−91°C (lit. 16 The 1 H NMR data matched the literature. 16 Assay of tert-Butyl Carbamate-Based Preformed Nitrogen Sources in the Oxyamination Reaction.…”

Section: ■ Results and Discussionsupporting

confidence: 74%

Osmium-Catalyzed Vicinal Oxyamination of Alkenes by N-(4-Toluenesulfonyloxy)carbamates

2012

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Section: ■ Results and Discussionsupporting

confidence: 74%

Osmium-Catalyzed Vicinal Oxyamination of Alkenes by N-(4-Toluenesulfonyloxy)carbamates

2012

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“…After 21 h the azide IR absorption completely disappeared in the reaction mixture ( Figure 1B), suggesting that all azide groups were converted into the aziridine adducts of C 60 . As well a new absorption was observed at 527 cm À1 assigned to the attached C 60 , [48] however, the other characteristic IR absorptions for the C 60 moiety were not detected due to an overlap with absorptions of PFS. The resulting C 60 -containing PFSs (3a-d) were purified by iterative reprecipitations into hexanes to remove unreacted C 60 and were obtained as brown powders in 52-63% isolated yields.…”

Section: Synthesis Of C 60 -Containing Pfsmentioning

confidence: 94%

“…The characteristic UV absorption and shoulder for 3b were also observed at 326 nm and 402 nm, respectively. [48] These absorptions originate from the C 60 moiety as shown in the inset of Figure 3, which shows the UV-vis spectrum for C 60 in toluene. PFS 3b was also characterized by 1 H, 13 C, and 29 Si NMR in benzene-d 6 .…”

Section: Characterization Of C 60 -Containing Pfsmentioning

confidence: 98%

Donor–Acceptor C₆₀‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices

Nanjo

Cyr

Liu

et al. 2008

Adv Funct Materials

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A series of polyferrocenylsilane (PFS) random copolymers containing covalently bound pendant [C60]fullerene groups, the first well‐characterized metallopolymers with pendant C60 units, have been prepared and characterized. The fullerene content of the prepared copolymers ranges from 7 to 24% relative to monomer unit. The desired copolymers were synthesized in three steps: metal‐catalyzed ring opening polymerization of sila[1]ferrocenophanes was performed to synthesize random copolymers of poly(ferrocenylmethylphenylsilane‐co‐ferrocenylchloromethylsilane); the resulting random PFSs were then functionalized by reaction with 11‐azido‐1‐undecanol to give PFSs with pendant azide groups; the desired donor–acceptor C60‐containing PFSs were then synthesized by the reaction of the azide group in the side chains with C60 in toluene at 110 °C. The resulting C60‐containing PFSs are air‐stable and soluble in aromatic solvents, chloroform, or THF. The UV‐vis spectra of these materials show broad absorption up to 800 nm. Thin films of these materials were examined as the active layer in rare examples of all solid‐state sandwich‐type diode devices based on ferrocene‐fullerene dyads. The devices exhibit photoconducting and photovoltaic responses, with an open circuit potential of ca. 0.3 V under white light illumination.

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“…Lebel Some papers concern functionalization of [60] fullerene [113,114]. Using nosyl 2,4,6-tri-tert-butylphenylhydroxamic acid in a biphasic system, a mixture of the expected aziridine or the corresponding oxazolidin-2-one was obtained [34,35].…”

Section: Other Nosyloxycarbamatesmentioning

confidence: 99%

Ethyl Nosyloxycarbamate: A Chameleonic Aminating Agent

Pellacani¹,

Fioravanti²,

Tardella

2011

COC

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The purpose of this review is to illustrate the use of ethyl nosyloxycarbamate (NsONHCO(2)Et). This is a versatile aminating agent known for over 47 years and used to generate, in the presence of organic or inorganic bases under homogeneous conditions, a carbonyl nitrene, a reactive intermediate able to form new C-N or X-N bonds by electrophilic amination reaction of a remarkable variety of nucleophilic substrates. Interest in this reagent has been renewed most recently, during the past dozen years. Operating still in alkaline medium, but under generally heterogeneous conditions, has made possible new synthetic applications for the conjugate base of the same nosyloxycarbamate. These, developed mainly by our research group, allow to carry out direct syntheses of various nitrogenated compounds under mild conditions. The applications span from simple molecules to highly functionalized compounds and many new exciting regio- and stereoselective routes can be envisioned. In particular, it was possible to obtain aziridines containing a cornucopia of assorted functions and therefore able to provide access to more complex molecules under simple operational conditions by using an aminating agent cheap and easy to obtain

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Aziridino[2′,3′ : 1,2][60]fullerene

Abstract: Thermal elimination of isobutene and C 0 2 from N-tert-butoxycarbonylaziridino[2',3': 1,21[60lfullerene 4 provides a clean and efficient route to aziridino[2',3': 1,21[60lfullerene 1, an isolable and stable solid.

Cited by 56 publications

References 6 publications

Osmium-Catalyzed Vicinal Oxyamination of Alkenes by N-(4-Toluenesulfonyloxy)carbamates

Osmium-Catalyzed Vicinal Oxyamination of Alkenes by N-(4-Toluenesulfonyloxy)carbamates

Donor–Acceptor C₆₀‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices

Ethyl Nosyloxycarbamate: A Chameleonic Aminating Agent

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Aziridino[2′,3′ : 1,2][60]fullerene

Abstract: Thermal elimination of isobutene and C 0 2 from N-tert-butoxycarbonylaziridino[2',3': 1,21[60lfullerene 4 provides a clean and efficient route to aziridino[2',3': 1,21[60lfullerene 1, an isolable and stable solid.

Cited by 56 publications

References 6 publications

Osmium-Catalyzed Vicinal Oxyamination of Alkenes by N-(4-Toluenesulfonyloxy)carbamates

Osmium-Catalyzed Vicinal Oxyamination of Alkenes by N-(4-Toluenesulfonyloxy)carbamates

Donor–Acceptor C60‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices

Ethyl Nosyloxycarbamate: A Chameleonic Aminating Agent

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Donor–Acceptor C₆₀‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices