4
112
L. L. R. Lorentz-Petersen et al.
SHORT PAPER
Dioctylamine19
Bp 139–141 °C/3 mbar (Lit. 145–155 °C/4 mbar).
(8) (a) Blank, B.; Michlik, S.; Kempe, R. Chem. Eur. J. 2009,
15, 3790. (b) Hamid, M. H. S. A.; Allen, C. L.; Lamb, G. W.;
Maxwell, A. C.; Maytum, H. C.; Watson, A. J. A.; Williams,
J. M. J. J. Am. Chem. Soc. 2009, 131, 1766. (c)Fujita, K.-i.;
Enoki, Y.; Yamaguchi, R. Tetrahedron 2008, 64, 1943.
(d) Yamaguchi, R.; Kawagoe, S.; Asai, C.; Fujita, K.-i. Org.
Lett. 2008, 10, 181. (e) Hollmann, D.; Tillack, A.; Michalik,
D.; Jackstell, R.; Beller, M. Chem. Asian J. 2007, 2, 403.
2
1
1
H NMR (300 MHz, CDCl ): d = 2.50 (t, J = 7.3 Hz, 4 H), 1.39 (m,
3
4
H), 1.20 (br s, 20 H), 0.79 (t, J = 6.7 Hz, 6 H).
1
3
C NMR (75 MHz, CDCl ): d = 50.1, 31.7, 30.1, 29.4, 29.2, 27.3,
3
2
2.5, 13.9.
MS (EI, 70 eV): m/z = 241 [M].
(
9) (a) Prades, A.; Corberán, R.; Poyatos, M.; Peris, E. Chem.
Eur. J. 2008, 14, 11474. (b) Hollmann, D.; Bähn, S.;
Tillack, A.; Beller, M. Chem. Commun. 2008, 3199.
Dicyclohexylamine8d
Bp 93–95 °C/5 mbar (Lit. 79–81 °C/0.5 mbar).
1
0e
(
c) Bähn, S.; Hollmann, D.; Tillack, A.; Beller, M. Adv.
1
H NMR (300 MHz, CDCl ): d = 2.55 (m, 2 H), 1.91–1.81 (m, 4 H),
3
Synth. Catal. 2008, 350, 2099. (d) Hollmann, D.; Bähn, S.;
Tillack, A.; Beller, M. Angew. Chem. Int. Ed. 2007, 46,
8291.
1
.76–1.67 (m, 4 H), 1.65–1.56 (m, 2 H), 1.32–0.95 (m, 10 H).
1
3
C NMR (75 MHz, CDCl ): d = 52.9, 34.2, 26.1, 25.2.
3
(
10) With Pt/C and Al, see: (a) Miyazawa, A.; Saitou, K.;
Tanaka, K.; Gädda, T. M.; Tashiro, M.; Prakash, G. K. S.;
Olah, G. A. Tetrahedron Lett. 2006, 47, 1437. With
PtCl (PPh ) and SnCl ·2H O, see: (b) Tsuji, Y.; Shida, J.;
MS (EI, 70 eV): m/z = 181 [M].
Acknowledgment
2
3 2
2
2
Takeuchi, R.; Watanabe, Y. Chem. Lett. 1984, 889. With
Pd/C, see: (c) Murahashi, S.-I.; Yoshimura, N.; Tsumiyama,
T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002. With
RuCl (PPh ) , see: (d) Khai, B. T.; Concilio, C.; Porzi, G.
We thank the Danish National Research Foundation for financial
support.
2
3 3
J. Organomet. Chem. 1981, 208, 249. With Raney nickel,
see: (e) De Angelis, F.; Grgurina, I.; Nicoletti, R. Synthesis
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Synthesis 2009, No. 24, 4110–4112 © Thieme Stuttgart · New York