2934
S.L. Jain et al. / Journal of Organometallic Chemistry 692 (2007) 2930–2935
and the chemical shifts are expressed in d parts per million
relative to tetramethylsilane (TMS) as internal standard.
The IR spectra were recorded on a Perkin Elmer FTIR X
1760 instrument. Mass spectra were recorded on Matrix
assisted laser desorption ionization (MALDI) mass
spectrometer.
References
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Benzylidine-tert-butylamine (Table 2, entry 1): Color-
less oil, IR (KBr) 3070, 2980, 1600, 1560, 1340,
(c) T. Welton, Chem. Rev. 99 (1999) 2071;
(d) J. Dupont, R.F. de Suza, P.A Z. Suarez, Chem. Rev. 102 (2002)
3667;
(e) P. Wasserscheid, W. Keim, Angew. Chem., Int. Ed. 39 (2000)
3772;
1135 cmÀ1 1H NMR (d ppm) 1.08 (s, 9H, (CH3)3C–),
.
4.60 (s, 1H), 7.00–7.60 (m, 5H, ArH) Mass m/z 165
(M++1).
(f) T. Welton, Ionic Liquids in Synthesis, in: P. Wasserscheid (Ed.),
VCH-Wiley, Weinheim, 2002.
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(b) H. Clavier, N. Audic, J.-C. Guillemin, M. Mauduit, J. Organomet.
Chem. 690 (2005) 3585;
Benzylidine-iso-propylamine (Table 2, entry 2): Color-
less oil, IR (KBr): 3060, 2978, 1590, 1345, 1138 cmÀ1
.
1H NMR (d ppm) 1.15–1.20 (d, 6H, (CH3)2CH–) 2.45
(sept, 1H, (CH3)3CH) 5.02 (s, 1H), 7.20–7.78 (m, 5H,
ArH); Mass m/z 151 (M++1).
(c) A.A. Valente, Eljko Petrovski, L.C. Branco, C.A.M. Afonso,
A.D. Lopes, C.C. Romao, C.D. Nunes, I.S. Gonc¸alves, J. Mol.
˜
Catal. A 218 (2004) 5;
Benzylidine–methylamine (Table 2, entry 3): Oil, IR
1
(KBr): 3062, 2980, 1602, 1140 cmÀ1. H NMR (d ppm)
2.80 (s, 3H, CH3, 4.25s, 1H), 7.27–7.77 (m, 5H, ArH); Mass
(d) F.E. Kuhn, J. Zhao, M. Abrantes, W. Sun, C.A.M. Afonso, L.C.
¨
m/z 123 (M++1).
Branco, I.S. Gonc¸alves, M. Pillinger, C.C. Romao, Tetrahedron
˜
Benzylidine–methylamine (Table 2, entry 3): Oil, IR
(KBr): 3060, 2979, 1600, 1230, 1140 cmÀ1. H NMR
(d ppm) 2.32 (s, 3H, CH3), 5.02 (s, 1H), 7.30–7.70
(m, 5H, ArH); Mass m/z 123 (M++1).
Lett. 46 (2005) 47.
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(1995) 2698;
p-Toluidine-tert-butylamine (Table 2, entry 4): Oil, IR
(KBr): 3065, 2976, 1575, 1341, 1132 cmÀ1 1H NMR
.
(b) F. Favre, H. Olivier, D. Commereuc, L. Saussine, Chem.
Commun. (2001) 1360.
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Dupont, Organometallics 17 (1998) 815.
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(b) J. Howarth, Tetrahedron Lett. 41 (2000) 6627;
(d ppm) 1.10 (s, 9H, (CH3)3C–), 2.30 (s, 3H, ArCH3),
4.62 (s, 1H), 7.16 (d, 2H, ArH), 7.35 (d, 2H, ArH); Mass
m/z 179 (M++1).
p-Toluidine–methylamine (Table 2, entry 5): Oil, IR
1
(KBr): 3065, 2976, 1575, 1341, 1132. H NMR (d ppm)
2.28 (s, 3H, ArCH3), 2.74 (s, 3H, CH3), 4.0–4.75 (s, 1H),
7.18 (d, 2H, ArH), 7.36 (d, 2H, ArH); Mass m/z 137
(M++1).
p-Anisidine-tert-butylamine (Table 2, entry 6): Oil, IR
(KBr): 3062, 2981, 1600, 1342, 1134 cmÀ1 1H NMR
.
(d ppm) 1.12 (s, 9H, (CH3)3C–), 4.50 (s, 1H), 3.75 (s, 3H,
OCH3), 7.20 (d, 2H, ArH), 7.39 (d, 2H, ArH); Mass m/z
195 (M++1).
´
´
(c) R. Alcantara, L. Canoira, P. Guilherme-Joao, P. Perez-Mendo,
p-Nitro-benzylidine-tert-butylamine (Table 2, entry 7):
m.p. 64–65 °C (lit 66 °C) [25]. IR (KBr) 3061, 2982, 1598,
Appl. Catal. A 218 (2001) 269;
(d) V. Farmer, T. Welton, Green Chem. 4 (2002) 97;
(e) I.A. Ansari, R. Gree, Org. Lett. 4 (2002) 1507;
(f) U.R. Pillai, Green Chem. 4 (2002) 170.
1340, 1137 cmÀ1
.
1H NMR (d ppm) 1.14 (s, 9H,
(CH3)3C–), 4.65 (s, 1H), 7.30 (d, 2H), 7.82 (d, 2H), Mass
m/z 210 (M++1).
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(2006) 263;
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Goncalves, Inorg. Chem. Commun. 6 (2003) 1228;
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3197;
p-Chloro-benzylidine-tert-butylamine (Table 2, entry 8):
m.p. 65–66 °C(lit 66–67 °C) [26]. IR (KBr) cmÀ13060, 2980,
1600, 1341, 1136. 1H NMR (d ppm) 1.12 (s, 9H), 4.26
(s, 1H) 7.28 (d2H), 7.75 (d, 2H); Mass m/z 200 (M++1).
Benzylidine–cyclohexylamine (Table 2, entry 9): Color-
1
less oil, IR (KBr) cmÀ1 3062, 2981, 1599, 1340, 1132. H
NMR (d ppm) 0.85–1.10 (m, 10H), 2.15 (m, 1H), 4.50–
4.82 (s, 1H), 7.82–7.32 (m, 5H, ArH); Mass m/z 171
(M++1).
(b) W.A. Herrmann, F.E. Kuhn, Acc. Chem. Res. 30 (1997) 169;
(c) F.E. Kuhn, A. Scherbaum, W.A. Herrmann, J. Organomet.
¨
Chem. 689 (2004) 4149;
(d) F.E. Kuhn, A.M. Santos, W.A. Herrmann, Dalton Trans. 15
¨
Furfurylidine-tert-butylamine (Table 2, entry10): Oil, IR
1
(KBr) cmÀ1 3106, 1587, 1479, 800. H NMR (d ppm) 1.12
(2005) 2483.
(s, 9H), 4.64 (s, 1H), 6.36 (dd,1H), 6.62 (d, 1H), 7.40
[14] W.A. Herrmann, R.W. Fischer, D.W. Marz, Angew. Chem. Int. Ed.
30 (1991) 1638.
(d, 1H); Mass m/z 156 (M++1).