K. B. Nolan, Inorg. Chim. Acta, 1986, 113, 27; C. A. Amodio and
D. J. Eastwood, Inorg. Chim. Acta, 1986, 122, L3; L. Maresca,
G. Natile, F. P. Intini, F. Gasparrini, A. Tiripicchio and
M. Tiripicchio-Camellini, J. Am. Chem. Soc., 1986, 108, 1180.
9 P. Braunstein, D. Matt, Y. Dusausay and J. Protas, J. Chem. Soc.,
Chem. Commun., 1979, 763; P. Braunstein, D. Matt, Y. Dusausay
and J. Fischer, Organometallics, 1983, 2, 1410; T. Uchiyama,
K. Takagi, K. Matsumoto, S. Ooi, Y. Nakamura and S. Klawaguchi,
Chem. Lett., 1979, 1197; T. Uchiyama, K. Takagi, K. Matsumoto,
S. Ooi, Y. Nakamura and S. Klawaguchi, Bull. Chem. Soc. Jpn.,
1981, 54, 1077.
10 J. Vicente, M. T. Chicote, M. A. Beswick and M. C. Ramirez de
Arellano, Inorg. Chem., 1996, 35, 6592; J. Vicente, M. T. Chicote,
M. C. Lagunas and P. G. Jones, Inorg. Chem., 1995, 34, 5441;
J. Vicente, M. T. Chicote, J. Fernández-Baeza and F. Lahoz, Inorg.
Chem., 1991, 30, 3617.
{N᎐C(Ph)O–N(CH Ph)–C(H)(Ph)}. Yield 74%. TLC on
᎐
2
SiO2, Rf = 0.72 (eluent CH2Cl2). IR spectrum (selected bands),
1
cmϪ1: 1667 s ν(C᎐N). H NMR spectrum in CDCl , δ: 4.10
᎐
3
(d, 12.9 Hz, 1H) and 4.40 (d, 12.2 Hz, 1H) (CH2Ph), 6.01 (s, br,
1H, N–CH–N), 7.26–7.50 (m, 12H), 7.55 (t, 7.5 Hz, 1H) and
8.00 (d, 7.3 Hz, 2H) (three Ph). 13C{1H} NMR spectrum in
CDCl3, δ: 63.1 (CH2Ph), 90.6 (N–CH–N), 126.4 (br), 128.33,
128.42, 128.46, 128.54 and 129.5 (CHo,m), 127.8, 128.1 and
131.9 (CHp), 133.8, 135.2 and 135.3 (Cipso) (three Ph), 161.6
(C᎐N).
᎐
{N᎐C(Ph)O–N(Me)–C(H)(C H Me)}. Yield 84%. TLC on
᎐
6
4
SiO2, Rf = 0.54 (eluent CH2Cl2). IR spectrum (selected bands),
1
cmϪ1: 1666 s ν(C᎐N). H NMR spectrum in CDCl , δ: 2.34 (s,
11 R. Ros, J. Renaud and R. Roulet, J. Organomet. Chem., 1976, 104,
271; Yu. N. Kukushkin and Yu. E. Larinova, Zh. Obshch. Khim.,
1994, 64, 1409.
᎐
3
3H, C6H4Me), 2.96 [s, C–N(Me)–O], 5.75 (s, br, 1H, N–CH–N),
7.17 (d, 7.8 Hz, 2H) and 7.34 (d, 8.1 Hz, 2H) (C6H4Me), 7.45 (t,
7.2 Hz, 2H), 7.53 (t, 7.5 Hz, 1H) and 7.99 (d, 7.0 Hz, 2H) (Ph).
13C{1H} NMR spectrum in CDCl3, δ: 21.1 (C6H4Me), 46.9
[br, C–N(Me)–O], 93.8 (br, N–CH–N), 126.5 (br), 128.4, 128.5,
128.6, 129.2, 131.9, 136.9 (br) and 138.1 (Ph and C6H4Me),
12 R. A. Michelin, R. Bertani, M. Mozzon, G. Bombieri, F. Benetollo
and R. J. Angelici, Organometallics, 1991, 10, 1751; R. A. Michelin,
R. Bertani, M. Mozzon, G. Bombieri, F. Benetollo and
R. J. Angelici, J. Chem. Soc., Dalton Trans., 1993, 959; R. A.
Michelin, M. Mozzon, P. Berin, R. Bertani, F. Benetollo,
G. Bombieri and R. J. Angelici, Organometallics, 1994, 13, 1341;
U. Belluco, R. Bertani, F. Meneghetti, R. A. Michelin, M. Mozzon,
G. Bandoli and A. Dolmella, Inorg. Chim. Acta, 2000, 300, 912.
13 R. A. Michelin, U. Belluco, M. Mozzon, P. Berin, R. Bertani,
F. Benetollo, G. Bombieri and R. J. Angelici, Inorg. Chim. Acta,
1994, 222, 21.
14 R. A. Michelin, M. Mozzon, R. Bertani, F. Benetollo, G. Bombieri
and R. J. Angelici, Inorg. Chim. Acta, 1994, 222, 327.
15 G. Wagner, A. J. L. Pombeiro and V. Yu. Kukushkin, J. Am. Chem.
Soc., 2000, 122, 3106.
16 G. Wagner, M. Haukka, J. J. R. Fraústo da Silva, A. J. L. Pombeiro
and V. Yu. Kukushkin, Inorg. Chem., 2001, 40, 264.
17 K. K. Andersen, Tetrahedron Lett., 1962, 93; J. Drabowicz,
B. Bujnicki and M. Mikołajczyk, J. Org. Chem., 1982, 47, 3325;
D. A. Evans, M. M. Faul, L. Colombo, J. J. Bisaha, J. Clardy
and D. Cherry, J. Am. Chem. Soc., 1992, 114, 5977; F. A. Davis,
R. ThimmaReddy, J. P. McCauley, Jr., R. M. Przeslawski,
M. E. Harakal and P. J. Carrol, J. Org. Chem., 1991, 56, 809;
F. A. Davis and M. C. Weismiller, J. Am. Chem. Soc., 1989, 111,
5964; G. Glahsl and R. Herrmann, J. Chem. Soc., Perkin Trans. 1,
1988, 1753.
18 J.-M. Brunel, P. Diter, M. Duetsch and H. B. Kagan, J. Org. Chem.,
1995, 60, 8086; F. Di Furia, G. Modena and R. Seraglia, Synthesis,
1984, 325.
19 H. L. Holland, Chem. Rev., 1988, 88, 473; S. Colonna, N. Gaggero,
P. Pasta and G. Ottolina, Chem. Commun., 1996, 2303; J. Tang,
I. Brackenridge, S. M. Roberts, J. Beecher and A. J. Willetts,
Tetrahedron, 1995, 51, 13217.
20 V. Yu. Kukushkin, V. K. Belsky, V. E. Konovalov, R. R. Shifrina,
A. I. Moiseev and R. A. Vlasova, Inorg. Chim. Acta, 1991, 183, 57.
21 V. Yu. Kukushkin, V. K. Belsky, V. E. Konovalov, G. A. Kirakosyan,
L. V. Konovalov, A. I. Moiseev and V. M. Tkachuk, Inorg. Chim.
Acta, 1991, 185, 143; V. K. Belsky, V. E. Konovalov, V. Yu.
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22 A. C. Cope and E. A. Caress, J. Am. Chem. Soc., 1966, 88, 1711.
23 H. Boucher and B. Bosnich, J. Am. Chem. Soc., 1977, 99, 6253.
24 L. Antolini, U. Folli, D. Iarossi, L. Schenetti and F. Taddei, J. Chem.
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25 G. Uccello-Barretta, R. Bernardini, R. Lazzaroni and P. Salvadori,
J. Organomet. Chem., 2000, 598, 174; G. Uccello-Barretta,
R. Bernardini, F. Balzano, R. Lazzaroni and P. Salvadori,
J. Organomet. Chem., 2000, 605, 68; P. Salvadori, G. Uccello-
Barretta, S. Bartozzi, R. Settambolo and R. Lazzaroni, J. Org.
Chem., 1988, 53, 5768.
160.1 (br, C᎐N).
᎐
{N᎐C(Ph)O–N(Me)–C(H)(C H OMe)}. Yield 91%. TLC on
᎐
6
4
SiO2, Rf = 0.49 (eluent CH2Cl2). IR spectrum (selected bands),
1
cmϪ1: 1662 s ν(C᎐N). H NMR spectrum in CDCl , δ: 2.97 [s,
᎐
3
C–N(Me)–O], 3.80 (s, 3H, C6H4OMe), 5.74 (s, br, 1H, N–CH–
N), 6.91 (d, 8.7 Hz, 2H) and 7.39 (d, 8.7 Hz, 2H) (C6H4OMe),
7.47 (t, 7.8 Hz, 2H), 7.54 (t, 7.8 Hz, 1H) and 8.01 (d, 7.8 Hz,
2H) (Ph). 13C{1H} NMR spectrum in CDCl3, δ: 46.7 [br,
C–N(Me)–O], 55.2 (C6H4OMe), 93.5 (br, N–CH–N), 113.9,
125.6, 127.8 (br), 128.44, 128.48, 128.52, 131.9 and 159.7 (Ph
and C H OMe), 160.5 (C᎐N).
᎐
6
4
Acknowledgements
G. W. is grateful to the FCT (Foundation for Science and
Technology) for fellowships (PRAXIS XXI BPD11779/97 and
SFRH BPD/1638/2000). We also thank Prof. R. Delgado
and Priv. Doz. Dr. R. Herrmann (both ITQB Oeiras) for
general support, Prof. V. Yu. Kukushkin for helpful discussion,
Prof. A. J. L. Pombeiro for putting some of his facilities at
our disposal, Mr H. Ferreira for giving us access to the NMR
facilities of the Instituto Superior Técnico, and Mr I. Marques
(Centro de Química Estrutural) for the FAB-MS measure-
ments.
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