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(a) Bertin, D.; Gigmes, D.; Marque, S. R. A. Recent Res. Dev. Org. Chem. 2006, 10, 63.
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Bertin, D.1
Gigmes, D.2
Marque, S.R.A.3
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Bacon, C.A.1
Cameron, N.R.2
Reid, A.J.3
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(c) Ciriano, M. V.; Korth, H.-G.; van Scheppingen, W. B.; Mulder, P. J. Am. Chem. Soc. 1999, 121, 6375.
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Ciriano, M.V.1
Korth, H.-G.2
van Scheppingen, W.B.3
Mulder, P.4
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9
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0031084556
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(d) Stipa, P.; Greci, L.; Carloni, P.; Damiani, E. Polym. Degrad. Stab. 1997, 55, 323.
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Stipa, P.1
Greci, L.2
Carloni, P.3
Damiani, E.4
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10
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3542996292
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Compare also: Bertin, D.; Gigmes, D.; Le Mercier, C.; Marque, S. R. A.; Tordo, P. J. Org. Chem. 2004, 69, 4925.
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(e) Compare also: Bertin, D.; Gigmes, D.; Le Mercier, C.; Marque, S. R. A.; Tordo, P. J. Org. Chem. 2004, 69, 4925.
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48349142457
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(b) Winter, R. A. E.; Galbo, J. P.; Seltzer, R.; Behrens, R. A.; Mar, A.; Schirmann, P. J.; Malherbe, R. F. EP 309402, 1989.
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(1989)
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Winter, R.A.E.1
Galbo, J.P.2
Seltzer, R.3
Behrens, R.A.4
Mar, A.5
Schirmann, P.J.6
Malherbe, R.F.7
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15
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48349135186
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See also ref. 5
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(b) See also ref. 5.
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33846287580
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(a) Nesvadba, P. Chimia 2006, 12, 832.
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(2006)
Chimia
, vol.12
, pp. 832
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Nesvadba, P.1
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17
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48349114635
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See also ref. 3a
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(b) See also ref. 3a.
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48349112248
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General Procedure for the Synthesis of N-Alkoxyamines Prostab 5198™ (2.50 g, 14.5 mmol) was dissolved in 4-heptanone (18.5 mL, 132.2 mmol, and 30% aq H2O2 (10 mL, 97.1 mmol) was added dropwise. Upon cooling to 10 °C, CuCl (100 mg, 7 mol, was added. The reaction mixture was stirred overnight at r.t. to give a greenish solution. A peroxide test conducted at this stage indicated no residual H2O2. EtOAc (80 mL) was added and the two phases were separated. The organic phase was washed successively with 10% ascorbic acid soin, H2O, 10% Na2CO3 soln, and brine. After drying over sodium sulfate and removal of the solvent, a green-brown oil was obtained. The product was purified by column chromatography on SiO2 (hexane-EtOAc, 15:1) to afford 1.75 g (60, of 1-propoxy-2,2,6,6- tetramethylpiperidin-4-ol; off-white solid. 1H NMR 400 MHz, CDCl3, δ
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+.
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22
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48349116685
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Commercial Product of Ciba Inc
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Commercial Product of Ciba Inc.
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23
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48349097064
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TEMPO works equally well. This method should also be applicable to other nitroxyl radicals
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TEMPO works equally well. This method should also be applicable to other nitroxyl radicals.
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25
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84932727448
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and references cited therein. See also
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(b) See also: Kirillov, A. I. Zh. Org. Khim. (Engl. Transl.) 1966, 2, 1048; and references cited therein.
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(1966)
Zh. Org. Khim. (Engl. Transl.)
, vol.2
, pp. 1048
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Kirillov, A.I.1
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26
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48349099829
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Dussault, P. Reactions of Hydroperoxides and Peroxides, In Active Oxygen in Chemistry, 2; Search Series, Chapman and Hall: London, 1995, 150.
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Dussault, P. Reactions of Hydroperoxides and Peroxides, In Active Oxygen in Chemistry, Vol. 2; Search Series, Chapman and Hall: London, 1995, 150.
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48349131322
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General Procedure for the Synthesis of N-Alkoxyamines Using Solvents Prostab 5198™ (8.6 g, 49.9 mmol) was added to toluene (100 mL, followed by 1-methoxyacetone (11.0 g, 2.5 equiv) and CuCl (125 mg, 2.5 mol, The mixture was stirred well while adding 30% aq H2O 2 (17.8 mL, 3.5 equiv) over a period of 1 h. The reaction mixture was stirred at r.t. overnight. Workup: as reported in ref. 8. Yield 8.89 g (82, of 1-methoxymethyl-2,2,6,6-tetrarnethylpiperidin-4-ol, off-white solid; NOCH 2OMe/NOMe ratio, ca. 13.5:1. 1H NMR (300MHz, CDCl 3, δ, 4.01 (m, 1 H, 3.82 (s, 3 H, 1.89 (dd, J, 14.2,3.6 Hz, 2 H, 1.82 (br s, 1 H, 1.67 (dd, J, 11.0, 3.6 Hz, 2 H, 1.21 (2 s, 6 H, 1.15 (2 s, 6 H, 13C NMR (75 MHz, CDCl3, δ, 103.1 (s, 63.5 (2q, 60.1 (t, 56.9 (p, 48.6 (2s, 33.7 (2 p, 21.5 (2 p, IR neat, 3239, 3005, 2972, 2933, 1467, 1363, 1343, 1245, 1148, 1
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48349097053
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General Procedure for the Synthesis of N-Alkoxyamines under Acidic Condition144, 116, 56, 36s Prostab 5198™ (25.1 g, 145.1 mmol) was dissolved in 2-butanone (105 mL, and 30% aq H2O 2 (50.0 mL, 485.3 mmol, ca. 3 equiv) was added over 10 min. Upon cooling to 5 °C, CuCl (0.71 g, 7.2 mmol, 5 mol, was added and the temperature was kept between 10 °C and 15 °C After 15-30 min, the pH of the reaction mixture was slowly adjusted to ca. 3.2 using 1 N HCl. The brownish solution was stirred overnight at r.t. while keeping the pH value at around 3.5 using a dosimat. A green homogeneous solution was obtained after 12 h. Workup: as reported in ref. 8. Yield: 22.9 g (114 mmol, 78, of 1-ethoxy-2,2,6,6- tetramethyl-piperidin-4-ol, solid, NOEt/NOMe ratio, ca. 9:1. 1H NMR (400 MHz, CDCl3, δ, 3.93 (dddd, J, 14.4, 11.6, 5.6, 3.6 Hz, 1 H, 3.77 (q, J, 9.6 Hz, 2 H, 1.81 dd, J, 14.4, 5.6
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(a) Molawi, K.; Schulte, T.; Siegenthaler, K. O.; Wetter, C.; Studer, A. Chem. Eur. J 2005, 11, 2335.
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Chem. Eur. J
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, pp. 2335
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Molawi, K.1
Schulte, T.2
Siegenthaler, K.O.3
Wetter, C.4
Studer, A.5
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(b) Teichert, A.; Jantos, K.; Harms, K.; Studer, A. Org. Lett. 2004, 6, 3477.
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(2004)
Org. Lett
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, pp. 3477
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Teichert, A.1
Jantos, K.2
Harms, K.3
Studer, A.4
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(d) Braslau, R.; Burrill, L. C. I. I.; Siano, M.; Naik, N.; Howden, R. K. Macromolecules 1997, 30, 6445.
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(1997)
Macromolecules
, vol.30
, pp. 6445
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Braslau, R.1
Burrill, L.C.I.I.2
Siano, M.3
Naik, N.4
Howden, R.K.5
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0032136305
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(e) Matyjaszewski, K.; Woodworm, B. E.; Zhang, X.; Gaynor, S. G.; Metzner, Z. Macromolcules 1998, 31, 5955.
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(1998)
Macromolcules
, vol.31
, pp. 5955
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Matyjaszewski, K.1
Woodworm, B.E.2
Zhang, X.3
Gaynor, S.G.4
Metzner, Z.5
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