P. Sharma et al. / Inorganic Chemistry Communications 9 (2006) 82–85
85
74.0 (C–Sb, C5H3), 91.12 (C, C5H3), 127.91 (C, Ph), 128.28 (C, Ph),
135.93 (C, Ph), 136.81 (C–Sb).
Acknowledgment
[19] Compound 2 was synthesized as compound 1, Fc(Me)NLi was used
in place of FcNLi. Yield 55%; m.p.: 60–61 ꢁC; IR (m cmÀ1): 453 (Sb–
C), 3060 (C–H aromatic) FAB+ (m/z): 531(100%) [M]+, 502(6%)
[M À Me2]+, 487 (62%) [M À NMe2]+, 454 (28%) [M À Ph]+ 410
Authors are thankful to DGAPA UNAM for financing
the project IN 210905.
(16%) [M À Ph À NMe2]+, 275(14%) [SbPh2]+
,
257(13%)
References
[FcCHMeNMe2]+
;
1H NMR (CDCl3, d ppm) 1.15 (d, 3H, CH3),
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Yamaguchi, Tetrahedron 56 (2000) 8833.
1.73 (s, 6H, NMe2), 3.84 (q, 1H, CH), 4.00 (s, 5H, C5H5), 4.12 (t, 1H,
C5H3), 4.20 (m, 1H, C5H3), 4.30 (m, 1H, C5H3), 7.23–7.58 (m, 10H,
Ph); 13C NMR (CDCl3, ppm) : 7.50 (Me), 38.66 (NMe2), 59.30 (CH),
68.89 (C, C5H5), 68.99 (CH, C5H3), 69.31 (CH, C5H3), 72.06 (CH,
C5H3), 74.68 (C–Sb, C5H3), 96.04 (C, C5H3), 127.84 (C, Ph), 128.09
(C, Ph), 128.17 (C, Ph), 136.57 ( C–Sb).
[20] In a schlenk tube, to a solution of stibine 1 (1.9 mmol) in CH2Cl2
(20 ml), was added CH3I (8.03 mmol) with continuous stirring. The
reaction was stirred for 24 h and the solution was concentrated under
vacuum to obtain a orange product which was isolated by filtration.
The compound was recrystallized from ethanol. Yield: 93%; m.p.:
120 ꢁC; IR (m cmÀ1): 462 (Sb–C), 3058 (C–H aromatic); FAB+ m/z :
1064(6%) [2M]+, 946(16%) [2M À 2NMe3]+, 532(95%) [M]+, 473
(36%) [M À NMe3]+, 454 (21%) [M À Ph]+, 397 (29%)
[M À Ph À NMe2]+, 275 (31%) [SbPh2]+ ; 242(12%) [FcCH2NMe2]+;
1H NMR (CDCl3, d ppm) 3.12 (s, 9H, NMe3), 4.05(d2 JHH, 12.5 Hz,
1H, CH2), 4.30 (d2 JHH, 12.4 Hz, 1H, CH2), 4.58 (m, 1H, C5H3), 4.20
(s, 5H, C5H5), 5.05 (t, 1H, C5H3), 5.53 (m, 1H, C5H3), 7.29–7.56 (m,
10H, Ph); 13C NMR (CDCl3, ppm) 52.87 (NMe3), 68.08 (CH2), 70.40
(C, C5H5), 74.29 (CH, C5H3), 76.02 (CH, C5H3), 76.98 (CH, C5H3),
78.28 (C–Sb C5H3), 93.28 (C, C5H3) 128.92 (C, Ph), 129.35 (C, Ph),
135.79 (C,Ph), 136.57 (C–Sb).
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Toscano, F. Lara, S. Hernandez, G. Espinosa, J. Organomet. Chem.
689 (2004) 2583.
[14] R.M. Gomez, P. Sharma, J.L. Arias, J.F. Perez, L. Velasco, A.
Cabrera, J. Mol. Catal. 170 (2001) 271.
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(1997) 677.
[15] P. Sharma, A. Cabrera, M. Sharma, C. Alvarez, N. Rosas, J.L. Arias,
R.M. Gomez, S. Hernandez, Z. Anorg. Allg. Chem. 626 (2000) 2330.
[16] P. Sharma, N. Rosas, A. Cabrera, A. Toscano, M.J. Silva, D. Perez,
L. Velasco, J. Perez, R. Guiterrez, J. Organomet. Chem. 690 (2005)
3286.
[22] B.W. Rockett, G. Marr, J. Organomet. Chem. 416 (1991) 327.
[23] Crystal data. Compound 1: crystal dimensions 0.368 · 0.178 ·
0.034 mm3, empirical formula = C25H26FeNSb, Fw = 518.07, triclinic,
ꢀ
space group P1, a = 7.7115(4), b = 10.3465(5), c = 14.6537(7),
3
˚
a = 70.184(1), b = 82.810(1), c = 83.632(1),V = 1088.35(9) A , Z = 2,
[17] J. Vela, P. Sharma, A. Cabrera, C. Alvarez, N. Rosas, S. Hernandez,
A. Toscano, J. Organomet. Chem. 634 (2001) 5.
Dc = 1.581 mg/m3, l = 1.917, F(000) = 520, independent reflec-
tions = 7761, R[I>2r(I)] = 0.0456. D/r = 1.123/À0.379 e AÀ3, GOF =
˚
[18] In a Schlenk tube a solution of Ph2SbCl (1.0 mmol) in anhydrous
THF (10 ml) was added dropwise under a nitrogen atmosphere to 2-
FcNLi (1.1 mmol) which was synthesized in situ according to
reported method [26] at À20 ꢁC with continuous stirring. The mixture
was further stirred for 24 h at room temperature (r.t.) and then
reaction was quenched with ice. After extraction with dichlorometh-
ane (3 · 10 ml) and drying over sodium sulfate, solvent was removed
under vacuum. Slow concentration from chloroform solution gives
the orange crystalline compound. Yield: 60%; m.p.: 90–91 ꢁC; IR
(m cmÀ1): 458 (Sb–C), 3057 (C–H aromatic) FAB+ m/z 517 (95%)
[M]+, 473(36%) [M À NMe2]+, 440 (17%) [M À Ph]+, 397 (29%)
[M À Ph À NMe2]+, 275(9%) [SbPh2]+, 242(18%) [FcCH2NMe2]+; 1H
NMR (CDCl3, d ppm) 1.91 (s, 6H, NMe2), 3.03 (d2 JHH, 12.7 Hz, 1H,
CH2), 3.66 (d2 JHH, 12.9 Hz, 1H, CH2), 3.79 (m, 1H, C5H3), 3.98 (s,
5H, C5H5), 4.20 (t, 1H, C5H3), 4.31 (m, 1H, C5H3), 7.19–7.59 (m,
10H, Ph); 13C NMR (CDCl3, ppm) 44.78 (NMe2), 59.91 (CH2), 69.28
(C, C5H5), 69.97 (CH, C5H3), 71.96 (CH, C5H3), 72.48 (CH, C5H3),
0.999. CCDC No. = 280195; Compound 2: crystal dimensions
0.346 · 0.322 · 0.142 mm3,
empirical
formula = C26H28FeNSb,
ꢀ
Fw = 532.09, triclinic, space group P1, a = 8.0351(4), b = 10.8605(6),
c = 13.7936(8), a = 74.648(1), b = 89.276(1), c = 81.366(1) V =
3
1147.0(1) A , Z = 2, Dc = 1.541 mg/m3, l = 1.917, F(000) = 536,
˚
independent reflections = 8168, R[I>2r(I)] = 0.0445, D/r = 1.000/
À0.507 e AÀ3, GOF = 0.990. CCDC No. = 280196; Compound 3:
˚
crystal dimensions 0.214 · 0.192 · 0.078 mm3, empirical formula =
C
28H35FeINOSb, Fw = 706.07, monoclinic, space group P21/n, a =
15.3782(8), b = 13.2581(7),c = 15.7316(8), a = 90, b = 118.975(1),
3
c = 90, V = 2806.0(3) A , Z = 4, Dc = 1.671 mg/m3, l = 2.600,
˚
F(000) = 1392, independent reflections = 10163, R[I>2r(I)] = 0.0456.
D/r = 1.612/À0.733 e AÀ3, GOF = 1.009, CCDC No. = 280197.
˚
[24] P. Stepnicka, I. Cisarova, Organometallics 22 (2003) 1728.
[25] J. Emsley, The Elements, third ed., Clarendon, Oxford, 1998.
[26] D. Marquarding, H. Klusacek, G. Gokel, P. Hoffmann, I. Ugi, J. Am.
Chem. Soc. 92 (1970) 5389.