K. H. Pannell et al.
ARTICLE
pdf/additives/World_of_Organotin_Chemicals.pdf, Accessed: 04/
2011.
= 0.2188 for all data (number of parameters = 209); R1 = 0.1191, wR2
= 0.1985 for 2354 reflections [I Ͼ 2σ(I)], Goof = 1.221. T = 298(2)
K
[2] Tin Chemistry: Fundamentals, Frontiers and Applications (Eds.:
A. G. Davies, M. Gielen, K. H Pannell, E. R.T Tiekink), John
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[2-(Methylselenenyl)benzyl)]phenyldichlorostannane (3Se). Yield
80%; m.p. 88–90 °C. 1H NMR (CDCl3): δ = 2.07 (s, 3 H, Ar-Se-
CH3), 3.29 (s, 2 H, Ar-CH2-Sn), 7.46–7.11 (m, 14 H, Ph, Ar). 13C
NMR (CDCl3): δ = 10.84 (1C, CH3-Se-Ar), 39.03 (1C, Ar-CH2-Sn),
127.57, 128.39, 129.18 (2C, Ph-Sn), 129.48, 130.80, 130.97, 131.32,
134.38 (2C, Ph-Sn), 137.81, 141.42 (1C, ipso-Ph-Sn). 77Se NMR
(CDCl3): δ = 151.78. 119Sn NMR (CDCl3): δ –58.10 ppm.
[4] T. Munguia, M. López-Cardoso, F. Cervantes-Lee, K. H. Pannell,
Inorg. Chem. 2007, 46, 1305–1314.
[5] A. J. Mukherjee, S. S. Zade, H. B. Singh, R. B. Sunoj, Chem. Rev.
2010, 87,110, 4357–4416.
[6] A. L. Braga, D. S. Lüdtke, F. Vargas, Curr. Org. Chem. 2006, 10,
1921–1938.
SC-XRD: C14H14Cl2SeSn, Fwt = 450.8 g·mol–1, a = 17.025(6) Å, b =
11.097(4) Å, c = 18.104(6) Å, β = 115.579(4)°, V = 3085.1(18) Å3,
monoclinic, P21/n, Z = 8, ZЈ = 4 F(000) = 1728, μ = 4.342 mm–1.
30915 total reflections, 6055 unique reflections [Rint = 0.0987]. R1 =
0.1213; wR2 = 0.2166 for all data (number of parameters = 320); R1
= 0.0792, wR2 = 0.1924 for 4108 reflections [I Ͼ 2σ(I)], Goof = 1.147.
T = 298(2(K)
[7] TEMC refers to an environment, in which the four covalent-
bonded substituents are in an arrangement closer for a tetrahedral
arrangement than for a TBP. In other words, it has less than 50%
of TBP character. The same applies to TEBC but now in contrast
to a octahedral arrangement.
[8] For tetrahedral or TBP arrangements Σax refers to the sum of
the angles formed by the substituents with the atom anti to the
nucleophile, Σeq is the sum of the angles formed by the substitu-
ents pushed by the nucleophile and ΣNu is the summatory of the
angles generated by the nucleophile (Se) with the substituents in
the attacked face. For tetrahedral the parameters are Σax = Σeq =
328.2° and ΣNu = 211.6°, whereas for TBP they are Σax = 270,
Σeq = 360° and ΣNu = 270°.
Crystallographic data (excluding structure factors) for the structures in
this paper have been deposited with the Cambridge Crystallographic
Data Centre, CCDC, 12 Union Road, Cambridge CB21EZ, UK. Copies
of the data can be obtained free of charge on quoting the depository
numbers CCDC-869513, CCDC-869514, and CCDC-869515 (1Se–3S)
(Fax: +44-1223-336-033; E-Mail: deposit@ccdc.cam.ac.uk, http://
www.ccdc.cam.ac.uk).
[9] P. J. Smith, A. P. Tupcˇiauskas, Annu. Rep. NMR Spectrosc. 1978,
8, 292–370.
[10] B. Wrackmeyer, Annu. Rep. NMR Spectrosc. 1985, 16, 73–186.
[11] A. Lari, C. Bleiholder, F. Rominger, R. Gleiter, Eur. J. Org. Chem.
2009, 2765–2774.
Acknowledgement
[12] M. Iwaoka, T. Katsuda, H. Komatsu, S. Tomoda, J. Org. Chem.
We thank the Robert Welch Foundation of Houston, Texas, for support
of this research through grant # AH–0546.
2005, 70, 321–327.
[13] G.M Sheldrick, SHELXTL v6.10, SMART, Bruker AXS, Inc.,
Madison, WI, USA, 2000 .
References
Received: March 05, 2012
[1] J. M. Batt, in: The World of Organotin Chemicals: Applications,
Published Online:
6
© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 2012, 1–7