Abstract
Three N -alkoxyamines were synthesized for use in nitroxide-mediated radical polymerization. Upon thermolysis, they generate new acyclic α-hydrogen nitroxides: one adamantyl substituted and two diol-containing nitroxides. The initiators were tested in polymerization reactions in direct comparison with the initiator derived from the nitroxide TIPNO.
Key words
nitroxide - nitrone - free radicals - polymers - Grignard reaction
References
1a Bosman AW.
Vestberg R.
Heumann A.
Frechet JMJ.
Hawker CJ.
J. Am. Chem. Soc.
2003,
125:
715
1b Hawker CJ.
Bosman AW.
Harth E.
Chem. Rev.
2001,
101:
3661
2a Patten TE.
Xia JH.
Abernathy T.
Matyjaszewski K.
Science
1996,
272:
866
2b Kato M.
Kamigaito M.
Sawamoto M.
Higashimura T.
Macromolecules
1995,
28:
1721
2c Percec V.
Barboiu B.
Macromolecules
1995,
28:
7970
2d Granel C.
Dubois P.
Jerome R.
Teyssie P.
Macromolecules
1996,
29:
8576
2e Wayland BB.
Basickes L.
Mukerjee S.
Wei ML.
Fryd M.
Macromolecules
1997,
30:
8109
2f Ando T.
Kamigaito M.
Sawamoto M.
Macromolecules
1998,
31:
6708
2g Collins JE.
Fraser CL.
Macromolecules
1998,
31:
6715
2h Percec V.
Barboiu B.
vanderSluis M.
Macromolecules
1998,
31:
4053
2i Moineau G.
Granel C.
Dubois P.
Jerome R.
Teyssie P.
Macromolecules
1998,
31:
542
3a Chiefari J.
Chong YK.
Ercole F.
Krstina J.
Jeffery J.
Le TPT.
Mayadunne RTA.
Meijs GF.
Moad CL.
Moad G.
Rizzardo E.
Thang SH.
Macromolecules
1998,
31:
5559
3b Mayadunne RTA.
Rizzardo E.
Chiefari J.
Chong YK.
Moad G.
Thang SH.
Macromolecules
1999,
32:
6977
3c Mayadunne RTA.
Rizzardo E.
Chiefari J.
Krstina J.
Moad G.
Postma A.
Thang SH.
Macromolecules
2000,
33:
243
4 Benoit D.
Chaplinski V.
Braslau R.
Hawker CJ.
J. Am. Chem. Soc.
1999,
121:
3904
5 Grimaldi S.
Finet JP.
Le Moigne F.
Zeghdaoui A.
Tordo P.
Benoit D.
Fontanille M.
Gnanou Y.
Macromolecules
2000,
33:
1141
6a Schulte T.
Studer A.
Macromolecules
2003,
36:
3078
6b Aldabbagh F.
Dervan P.
Phelan M.
Gilligan K.
Cunningham D.
McArdle P.
Zetterlund PB.
Yamada B.
J. Polym. Sci., Part A: Polym. Chem.
2003,
41:
3892
6c Marque S.
Sobek J.
Fischer H.
Kramer A.
Nesvadba P.
Wunderlich W.
Macromolecules
2003,
36:
3440
6d Bacon CA.
Cameron NR.
Reid AJ.
Macromol. Chem. Phys.
2003,
204:
1923
6e Wetter C.
Gierlich J.
Knoop CA.
Muller C.
Schulte T.
Studer A.
Chem.-Eur. J.
2004,
10:
1156
6f Nesvadba P.
Bugnon L.
Sift R.
J. Polym. Sci., Part A: Polym. Chem.
2004,
42:
3332
7a Detrembleur C.
Sciannamea V.
Koulic C.
Claes M.
Hoebeke M.
Jerome R.
Macromolecules
2002,
35:
7214
7b Marque S.
Fischer H.
Baier E.
Studer A.
J. Org. Chem.
2001,
66:
1146
7c Harth E.
Van Horn B.
Hawker CJ.
J. Chem. Soc., Chem. Commun.
2001,
823
7d Nesvadba P.
Bugnon L.
Sift R.
Polym. Int.
2004,
53:
1066
7e Studer A.
Harms K.
Knoop C.
Muller C.
Schulte T.
Macromolecules
2004,
37:
27
7f Cuatepotzo-Diaz R.
Albores-Velasco M.
Saldivar-Guerra E.
Jimenez FB.
Polymer
2004,
45:
815
8a Sár CP.
Osz E.
Jeko J.
Hideg K.
Synthesis
2005,
255
8b Sár CP.
Hideg .
Vass I.
Hideg K.
Bioorg. Med. Chem. Lett.
1998,
8:
379
9 Murray RW.
Jeyaraman R.
J. Org. Chem.
1985,
50:
2847
10 Dao J.
Benoit D.
Hawker CJ.
J. Polym. Sci., Part A: Polym. Chem.
1998,
36:
2161
11a Emmons WD.
J. Am. Chem. Soc.
1957,
79:
5739
11b Singh B.
J. Am. Chem. Soc.
1968,
90:
3893
11c Lee TD.
Keana JFW.
J. Org. Chem.
1976,
41:
3237
11d Christensen D.
Joergensen KA.
Hazell RG.
J. Chem. Soc., Perkin Trans. 1
1990,
2391
12 Use of THP as the hydroxy protecting group gives a more robust set of intermediates: Braslau, R.; Gonzalez, C., unpublished results from this laboratory.
13a Reznikov VA.
Gutorov IA.
Gatilov YV.
Rybalova TV.
Volodarsky LB.
Russ. Chem. Bull.
1996,
45:
384
13b Kotake Y.
Kuwata K.
Janzen EG.
J. Phys. Chem.
1979,
83:
3024
13c Chiarelli R.
Rassat A.
Rey P.
J. Chem. Soc., Chem. Commun.
1992,
1081
13d Ahrens B.
Davidson MG.
Forsyth VT.
Mahon MF.
Johnson AL.
Mason SA.
Price RD.
Raithby PR.
J. Am. Chem. Soc.
2001,
123:
9164
14 Marque S.
Fischer H.
Baier E.
Studer A.
J. Org. Chem.
2001,
66:
1146
15 d = 5.2 × 10-3 s-1 for the triol 13 , and BDE = 127.1 kJ/mol, Kd = 3.1 × 10-2 s-1 for TIPNO: Marque S.
J. Org. Chem.
2003,
68:
7582
16 Marque S.
Le Mercier C.
Tordo P.
Fischer H.
Macromolecules
2000,
33:
4403
17 Piotrowska H.
Serafin B.
Urba’nski T.
Tetrahedron
1963,
19:
379
18 Hawker CJ.
Barclay GG.
Dao J.
J. Am. Chem. Soc.
1996,
118:
11467
19 Braslau, R; Nilsen, A.; detailed studies on the decomposition of TIPNO will be reported in the near future.
20a Fischer H.
J. Am. Chem. Soc.
1986,
108:
3925
20b Daikh BE.
Finke RG.
J. Am. Chem. Soc.
1992,
114:
2938
20c Fischer H.
J. Polym. Sci., Part A: Polym. Chem.
1999,
37:
1885
21 Souaille M.
Fischer H.
Macromolecules
2002,
35:
248
22a Olah GA.
Krishnamurthy VV.
Iyer PS.
J. Org. Chem.
1983,
48:
3373
22b Smith GW.
Williams HD.
J. Org. Chem.
1961,
26:
2207
23 Cliffe IA.
Crossley R.
Shepherd RG.
Synthesis
1985,
1138
24 Kliegel W.
Preu L.
Chem.-Ztg.
1991,
115:
103
