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It has been previously reported that other 2,4-dinitrophenylhydrazones fail to give cycloaddition reactions. See: Yap, G. P. A, Alkorta, I, Jarerovic, N, Elguero, J. Aust. J. Chem. 2004, 57, 1103; and references therein
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It has been previously reported that other 2,4-dinitrophenylhydrazones fail to give cycloaddition reactions. See: Yap, G. P. A.; Alkorta, I.; Jarerovic, N.; Elguero, J. Aust. J. Chem. 2004, 57, 1103; and references therein.
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34248144801
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Compound 2b: A solution of p-nitrophenylhydrazine (1.0 g, 6.5 mmol, 3,5,5-trimethylhexanal (0.82 g, 6.5 mmol) and two drops of AcOH in EtOH (50 mL) was heated under reflux for 2 h. The solid was filtered off and recrystallized in EtOH to give 2b as a red solid (1.47 g, 82, mp 82.3-82.7 °C. 1H NMR (200 MHz, CDCl3, δ, 8.13 (d, J, 9.2 Hz, 2 H, 7.90 (s, 1 H, 7.19 (t, 1 H, 6.99 (d, J, 9.2 Hz, 2 H, 2.10-2.40 (m, 2 H, 1.85 (m, 1 H, 1.32 (dd, J1, 3.4 Hz, J2, 14.0 Hz, 1 H, 1.13 (dd, J1, 6.2 Hz, J2, 14.0 Hz, 1 H, 1.01 (d, J, 6.6 Hz, 3 H, 0.91 (s, 9 H, 13C NMR (50 MHz, CDCl3, δ, 150.3, 145.3, 144.5, 140.4, 139.7, 126.4, 126.3, 112.0, 111.3, 50.8, 50.6, 41.6, 35.7, 31.3, 31.3, 30.1, 28.2, 27.7, 23.0, 22.8. FT-IR ATR, 3289, 2941, 1617, 1511, 1335, 1266 cm-1. Anal. Calcd for C15H
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2: 995.98; found: 995.9.
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Delgado, J. L.; de la Cruz, P.; Lopez-Arza, V.; Langa, F.; Gan, Z.; Araki, Y.; Ito, O. Bull. Chem. Soc: Jpn. 2005, 78, 1500.
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Bull. Chem. Soc: Jpn
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Delgado, J.L.1
de la Cruz, P.2
Lopez-Arza, V.3
Langa, F.4
Gan, Z.5
Araki, Y.6
Ito, O.7
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0037462327
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Shackelford, S. A.; Anderson, M. B.; Christie, L. C.; Goetzen, T.; Guzman, M. C.; Hananel, M. A.; Kornreich, W. D.; Li, H.; Pathak, V. P.; Rabinovich, A. K.; Rajapakse, R. J.; Truesdale, L. K.; Tsank, S. M.; Vazir, H. N. J. Org. Chem. 2003, 68, 267.
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J. Org. Chem
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Shackelford, S.A.1
Anderson, M.B.2
Christie, L.C.3
Goetzen, T.4
Guzman, M.C.5
Hananel, M.A.6
Kornreich, W.D.7
Li, H.8
Pathak, V.P.9
Rabinovich, A.K.10
Rajapakse, R.J.11
Truesdale, L.K.12
Tsank, S.M.13
Vazir, H.N.14
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27
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34248188558
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Experimental Procedure: To an anhyd CH2Cl2 solution of the corresponding fullerene derivative 2 (1 equiv) in CH 2Cl2, tetramethylammonium nitrate (2 equiv) was added under Ar. The solution was cooled to the desired temperature and triflic anhydride (2 equiv) was added. NO2OTf was formed in situ and the solution was kept at this temperature until the complete disappearance of the starting material (the reaction progression was followed by TLC, The reaction was then quenched by adding a Na2CO3 solution (pH 8, The organic layer was separated, dried and evaporated. The remaining solid was purified by column chromatography affording the desired compounds 1a-d. Compound 1a: reaction temperature: -5°C for 4 h. Column chromatography (silica gel; toluene-hexane, 1:2, yield: 90, 1H NMR (500 MHz, CDCl3, δ, 8.80 (d, J, 2.5 Hz, 1 H, 8.45 dd, J
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4: 1140.86; found: 1141.2.
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0036315624
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Langa, F.; De la Cruz, P.; Delgado, J. L.; Espildora, E.; Gómez-Escalonilla, M. J.; De la Hoz, A. J. Mater. Chem. 2002, 12, 2130.
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J. Mater. Chem
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Langa, F.1
De la Cruz, P.2
Delgado, J.L.3
Espildora, E.4
Gómez-Escalonilla, M.J.5
De la Hoz, A.6
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29
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25144517721
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Ajamaa, F.; Figueira Duarte, T. M.; Bourgogne, C.; Holler, M.; Fowler, P. W.; Nierengarten, J. F. Eur. J. Org. Chem. 2005, 3766.
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(2005)
Eur. J. Org. Chem
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Ajamaa, F.1
Figueira Duarte, T.M.2
Bourgogne, C.3
Holler, M.4
Fowler, P.W.5
Nierengarten, J.F.6
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