SCOPUS 정보 검색 플랫폼

Volumn 8, Issue 26, 2006, Pages 6075-6078

Switch of electronic reactivity in fullerene C60: Activation of three trans-4 positions via temporary saturation of the cis-1 positions

(3) Chuang, Shih Ching a Khan, Saeed I a Rubin, Yves a

a UNIVERSITY OF CALIFORNIA (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE C60; FULLERENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; ELECTRON; MASS SPECTROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ELECTRONS; FULLERENES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 33846247881 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol0625637 Document Type: Article

Times cited : (7)

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- Synthesis of Tris-Bingel Bis-isobenzofuran C60 Adduct 3a. 9,10-Dimethylanthracene (102 mg, 0.497 mmol) was added to a solution of cis-1 adduct 2a (108 mg, 0.100 mmol) in toluene (250 mL) at ambient temperature under argon, and then the mixture was stirred for 2 h. Tetrabromomethane (593 mg, 1.79 mmol) and DBU (276.5 mg, 1.82 mmol) were then added. Dimethyl malonate (39 mg, 0.298 mmol) in toluene (10 mL) was injected slowly into the solution over 2 h using a mechanical syringe pump, and the mixture was stirred for 24 h at ambient temperature. The solvent was evaporated under reduced pressure, and the residue was dissolved in CS2. Flash chromatography on silica gel was performed using toluene as eluent to recover the starting material (27 mg, Slowly increasing the polarity of the eluent (toluene/EtOAc, from 90:1 to 30:1) eluted the tris-Bingel adduct 3a as a bright-orange solid: yield 18, 24% based on recovered starting material, R
- 14 1472.2, found 1472.9. See the Supporting Information for spectral data of compound 3b.

33
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- 1 = 0.066, Rw = 0.1758, GoF = 0.812.

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- Synthesis of Tris-trans-4-Bingel Adduct 4. A solution of tris-Bingel 3a (4 mg, 2.72 mmol) and C60 (195 mg, 0.271 mmol) in 1-chloronaphthalene (40 mL) was flushed with argon for 15 min and then heated under reflux for 30 min. The reaction mixture was cooled, hexanes (20 mL) were added, and then the mixture was passed through a short plug of silica gel. Toluene was used initially to elute out C60. Subsequently, a mixture of toluene and EtOAc (3:1) was used to obtain all of the polar materials. The solvent was evaporated under reduced pressure, and then the residue was submitted to chromatography (toluene then toluene/EtOAc, 60:1) to obtain the cis-1 adduct 2a (2.8 mg, Rf, 0.46 (toluene/EtOAc 20:1, The olive-green tris-Bingel adduct 4 was obtained in 86% yield after eluting with toluene/EtOAc (30:1, Compound 4: R f, 0.39 (toluene/EtOAc 20:1, 1H NMR (500 MHz, CDCl3) δ
- 12 1110.08, found 1110.05.

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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.