1 S. Oae and N. Furukawa, Sulfilimines and Related Derivatives, ACS,
Washington DC, 1983.
2 T. L. Gilchrist and C. J. Moody, Chem. Rev., 1977, 77, 409.
3 N. Furukawa, T. Yoshimura and S. Oae, Tetrahedron Lett., 1973,
2113.
4 T. Yoshimura, N. Furukawa, T. Akasaka and S. Oae, Tetrahedron, 1977,
33, 1061.
5 S. M. Aucott, M. R. Bailey, M. R. J Elsegood, L. M. Gilby,
K. E. Holmes, P. F. Kelly, M. Papageorgiou and S. Pedron-Haba,
New J. Chem., 2004, 959.
6 W. Clegg, S. H. Dale, D. Drennan and P. F. Kelly, Dalton Trans., 2005,
314.
7 M. R. J. Elsegood, P. F. Kelly, G. Reid and P. M. Staniland, Dalton
Trans., 2007, 1665.
Notes and references
‡ All reactions were performed under an atmosphere of dry nitrogen
using standard Schlenk techniques and appropriately dried solvents.
MSH was prepared by the literature route16 and Ph2Se used as received
(Aldrich). Safety note!: Solid MSH can spontaneously (and unpredictably)
decompose, resulting in an explosive pressure change. Samples should be
kept in small amounts in loosely sealed containers, thereby minimising the
risks should decomposition occur.
[Ph2Se(NH2)][mesSO3]. Ph2Se (0.902 g, 3.87 mmol) was dissolved in Et2O
(50 cm3), and MSH (1.04 g, 4.83 mmol) added as a solid in several portions.
The mixture was stirred vigorously overnight, after which the precipitate
formed was filtered under N2 and dried under reduced pressure. Yield:
1.232 g (71%). Microanalysis: found C 55.5, H 5.5, N 3.1%; C21H23NO3SSe
requires: C, 56.3; H, 5.2; N, 3.1%. mmax(KBr)/cm−1: 2970, 1476, 1448, 1226,
1171, 1085, 850, 754, 686, 584, 486; dSe (CD3OD) = 934 ppm.
8 A. D. M. Curtis, R. McCague, C. A. Ramsden and M. R. Raza, Chem.
Commun., 1999, 189.
[Ph2SeNSePh2][BPh4]. [Ph2Se(NH2)][mesSO3] (0.300 g, 0.67 mmol) was
dissolved in THF–MeCN (9 : 1, 15 cm3), and the solution temperature
reduced to ca. −50 ◦C, resulting in some precipitation of material. LDA
(0.33 cm3 of a 2 M solution, 0.67 mmol) was added with stirring; within
a minute all solid had dissolved leaving a clear, yellow solution, at which
point NBS (0.119 g, 0.67 mmol) was added. The resulting mixture was
stirred for ca. 2 min., after which Ph2Se (0.156 g, 0.67 mmol) was added.
After stirring for 1 h, the mixture was reduced to dryness, MeOH (2–3 cm3)
added, and an excess of Na[BPh4] (0.287 g, 0.84 mmol) added as a solid.
The mixture was stirred for 1 h, and the resulting precipitate filtered and
dried in vacuo. Yield 0.201 g (38%). Microanalysis: found C 72.6, H 5.4, N
2.2%; C48H40Se2BN requires C 72.1, H 5.0, N 1.8%; mmax(KBr)/cm−1: 3214,
3003, 1578, 1476, 1440, 1201, 1184, 1095, 1020, 844, 783, 730, 715, 683,
611, 600; dH (dmso) = 7.96 (d, 8H, 8 × PhSe Ar-H), 7.56 (br s, 12H, 12 ×
PhSe Ar-H), 7.23 (br s, 8H, 8 × BPh4 Ar-H), 6.96 (t, 8H, 8 × BPh4 Ar-H),
6.82 (t, 4H, 4 × BPh4 Ar-H); dC (dmso) = 163.6 ppm (1 : 1 : 1 : 1 q, BPh4
Ar-C), 139.8 (s, PhSe Ar-C), 135.5, 121.5 (s, BPh4 Ar-CH), 129.8 (s, PhSe
Ar-CH), 127.5 (s, PhSe Ar-CH) 125.3 (d, BPh4 Ar-CH); dSe (CDCl3) =
731 ppm. m/z (ES+): 481 (C24H20Se2N requires 481).
9 S. Oae, M. Fukumura and N. Furukawa, Phosphorus Sulfur Relat.
Elem., 1981, 10, 153; H. W. Roesky, K.-L. Weber, U. Seseke, W. Pimkert
and M. Noltemeyer, J. Chem. Soc., Dalton Trans., 1985, 565.
10 N. Kamigata, H. Taka, A. Matsuhisa, H. Matsuyama and T. Shimizu,
J. Chem. Soc., Perkin Trans. 1, 1994, 2257; T. Shimizu, N. Seki, H. Taka
and N. Kamigata, J. Org. Chem., 1996, 61, 6013.
11 T. Shimizu, N. Kamigata and S. Ikuta, J. Chem. Soc., Perkin Trans. 2,
1999, 1469.
12 (a) R. Appel and G. Bu¨chler, Z. Anorg. Allg. Chem., 1966, 348, 175;
(b) H. Horn and R. Paetzold, Z. Anorg. Allg. Chem., 1974, 404,
213.
13 S. M. Aucott, S. H. Dale, M. R. J Elsegood, L. M. Gilby, K. E. Holmes
and P. F. Kelly, Acta Crystallogr., Sect. C: Cryst. Struct. Commun.,
2005, 61, o112.
14 E.g. see K. E. Holmes, P. F. Kelly and M. R. J. Elsegood, Dalton Trans.,
2004, 3488 and references therein.
15 (a) E.g. T. Maaninen, R. Laitinen and T. Chivers, Chem. Commun.,
2002, 1812; (b) M. Bruncko, T. V. Khuong and K. B. Sharpless, Angew.
Chem., Int. Ed. Engl., 1996, 35, 454.
16 Y. Tamura, J. Minamikawa, K. Sumoto, S. Fujii and M. Ikeda, J. Org.
Chem., 1973, 38, 1239.
Crystal data for [Ph2SeNSePh2][BPh4]. C48H40BNSe2, M 799.54; triclinic,
¯
˚
˚
P1; a = 10.9985(4), b = 15.9145(6), c = 24.0519(10) A, a = 85.7218(6), b =
◦
76.9512(6), c = 71.9053(6) , Z = 4, V = 3898.4(3) A ; qcal = 1.362 g cm−3
;
3
17 Bruker Apex 2 and Saint; software for CCD diffractometers, Bruker
AXS Inc., Madison, WI, 2006.
l(Mo-Ka) = 1.931 mm−1; k = 0.71073 A, T = 150(2) K; 47137 reflections
were collected on a Bruker APEX 2 CCD diffractometer using narrow x-
scans, 24038 of which were independent (Rint = 0.0256).17,18 The structure
was solved by direct methods and refined on F2 values to give a final R =
0.0365 for 17868 data with F2 > 2r(F2); wR2 = 0.0918 for all data.19
˚
18 G. M. Sheldrick, SADABS v. 2007/2, University of Go¨ttingen,
Germany, 2007.
19 G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008,
64, 112.
3800 | Dalton Trans., 2008, 3798–3800
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