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Volumn , Issue 2, 2007, Pages 235-238

Synthesis of 2,2-[60]fullerenoalkylamines via the Curtius rearrangement

Author keywords

2,2 60 fullerenoalkanoyl azide; 2,2 60 fullerenoalkanoyl chloride; 2,2 60 fullerenoalkylamine; 60 fullerene; Curtius rearrangement

Indexed keywords

2,2 [60]FULLERENOALKYLAMINE DERIVATIVE; ALIPHATIC AMINE; AZIDE; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CURTIUS REARRANGEMENT; DECARBOXYLATION; SYNTHESIS;

EID: 33847034399 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968017 Document Type: Article

Times cited : (10)

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- For selected examples of cyclopropanated [60]fullerene with functional group (s), see: (a) Bingel, C. Chem. Ber. 1993, 126, 1957.
- For selected examples of cyclopropanated [60]fullerene with functional group (s), see: (a) Bingel, C. Chem. Ber. 1993, 126, 1957.

5
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11
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- The acyl chlorides 2b-g were synthesized by procedures similar to those reported in the literature4b (Scheme 2, Sulfonium Salts: The sulfonium tetrafluoroborates 5b-g were obtained from the corresponding tert-butyl 2-(methylthio)alkanoates by the reaction with trimethyloxonium tetrafluoroborate in CH2Cl2 at r.t. for 24 h, which were used without purification for further reactions. tert-Butyl [60]Fullerenoalkanoates: The solutions of [60]fullerene and the sulfonium tetrafluoroborates 5b-g were allowed to react with DBU, which should generate in situ sulfonium ylides 6b-g, in toluene-CH2Cl2 at r.t. for 18 h to give the tert-butyl [60]fullerenoalkanoates 7b-g 21-65% yields, 60]Fullerenoalkanoic Acids: The tert-butyl esters 7b-g thus-obtained were readily converted into the [60]fullerenoalkanoic acids 8b-g through the cleavage of the
- 2-1,4-dioxane under reflux for 5 h (84-99% yield). (Chemical Equation Presented)

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15
- 33847060361
- 2c: IR (KBr, 2923, 1776, 1509, 1453, 1428, 1185, 987, 794, 754, 694, 575, 525 cm-1. 1H NMR [300 MHz, CDCl 3-CS2 (1:1, δ, 1.61 (t, J, 7.4 Hz, 3 H, 3.10 (q, J, 7.4 Hz, 2 H, MS (MALDI-TOF; dithranol, m/z [M, calcd for C64H5ClO: 824.00; found: 824.11. 2f: IR (KBr, 2925, 1779, 1509, 1427, 1252, 1172, 1044, 1030, 754, 698, 575, 526 cm-1. 1H NMR [300 MHz, CDCl3-CS 2 (1:1, δ, 3.91 (s, 3 H, 7.10 (d, J, 8.7 Hz, 2 H, 8.03 (d, J, 8.7 Hz, 2 H, MS (MALDI-TOF; dithranol, m/z [M, calcd for C69H7ClO2: 902.01; found: 902.02, Chemical Equation Presented) 2g: IR (KBr, 2955, 1778, 1495, 1426, 1210, 1185, 1044, 819, 807, 754, 697, 576, 525 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.29 d, J, 6.6 Hz, 6 H, 2
- 3): δ = 23.94, 33.74, 62.56, 75.23, 127.03, 127.09, 127.44, 127.79, 133.23, 137.03, 137.70, 138.40, 140.90, 140.98, 141.78, 141.96, 142.01, 142.07, 142.68, 142.77, 142.83, 142.87, 143.47, 143.68, 144.23, 144.35, 144.39, 144.50, 144.53, 144.63, 144.69, 144.76, 145.02, 145.06, 145.09, 145.16, 145.56, 148.76, 166.80.

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