4
86
J. BINDER ET AL.
27.5, 127.4 ppm. 29Si NMR (59.64 MHz, C6D6): δ −33.9 ppm. Funding
1
+
MS (70 eV, m/z) = 336.1 (M )
This work was supported by the NAWI Graz project, collaboration between
the Graz University of Technology and the Graz University.
-Naphthyl SiH (8)
6
g 1-naphthyl2SiCl2 (16.9 mmol, 1 equiv.) in 100 mL Et2O
References
and 20 mL THF. 0.7 g LiAlH4 pellets (18.4 mmol, 1.2 equiv.)
in 100 mL Et2O. 150 mL degassed H2SO4 (10%). Crystals suit-
1
2
3
. Riedel, R.; Mera, G.; Hauser, R.; Klonczynski, A. J. Ceram. Soc. Jpn.
006, 114(1330), 425-444.
. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis,
nd ed.; John Wiley and Sons, Inc.: New York, 1991.
. Kocienski, P. J. Protecting Groups, Vol. 3; Thieme: Stuttgart, 1994.
2
able for X-ray diffraction analysis were grown from toluene at
1
4
°C. Yield 59% (2.85 g, 10.3 mmol). mp = 98–99°C. H NMR
2
(
300 MHz, C6D6): δ 8.20 (m, 2H), 7.70 (d, 2H), 7.64 (d, 2H), 7.61
1
1
29
(
m, 2H), 7.23–7.20 (m, 4H), 7.11 (dd, 2H), 5.72 (s, J( H- Si)
4. Minge, O.; Nogai, S.; Schmidbaur, H. Z. Naturforsch., B: Chem. Sci.
004, 59, 153-160.
199.5 Hz, 2H) ppm. 13C NMR (75.5 MHz, C6D6): δ 137.7,
2
=
5
6
7
8
. Gooding, J. J.; Ciampi, S. Chem. Soc. Rev. 2011, 40(5), 2704-2718.
. Chatgilialoglu, C. NATO ASI Ser., Ser. C. 1989, 260, 115-123.
. Denmark, S. E.; Ober, M. H. Aldrichim. Acta. 2003, 36, 75-85.
. Feigl, A.; Bockholt, A.; Weis, J.; Rieger, B. Silicon Polymers; Springer:
Berlin, Heidelberg, 2011; pp. 1-31.
1
36.9, 133.4, 130.9, 129.6, 128.8, 127.9, 126.4, 125.8, 125.3 ppm.
29
Si NMR (59.64 MHz, C6D6): δ −39.3 ppm. MS (70 eV, m/z) =
+
284.1 (M ).
9
. Lauterbur, P. C. Determination of Organic Substances by Physical Meth-
ods; Academic Press: New York, 1962; pp. 465-533.
,-Xylyl SiH (9)
10. Danilenko, T. N.; Tatevosyan, M. M.; Vlasenko, V. G. J. Struct. Chem.
4
g 2,4-xylyl2SiCl2 (12.9 mmol, 1 equiv.) in 40 mL Et2O, 0.59 g
2012, 53, 876-884.
LiAlH4 pellets (15.5 mmol, 1.2 equiv.) in 100 mL Et2O. 50 mL
degassed H2SO4 (10%). The resulting solid was recrystallized
11. Schäfer, A.; Saak, W.; Haase, D.; Müller, T. Angew. Chem., Int. Ed. 2012,
5
1, 2981-2984.
1
1
2. Lambert, J. B.; Stern, C. L.; Zhao, Y.; Tse, W. C.; Shawl, C. E.; Lentz, K.
T.; Kania, L. J. Organomet. Chem. 1998, 568, 21-31.
from toluene to obtain colorless crystals. Yield 61% (1.89 g,
1
7
.87 mmol), mp = 46–47°C. H NMR (300 MHz, C6D6): δ
3. Rofouei, M. K.; Lawless, G. A.; Morsali, A.; Hitchcock, P. B. Anal. Sci.:
X-ray Struct. Anal. Online, 2005, 21, x103-x104.
7
.51 (d, 1H), 6.87 (d, 1H), 6.83 (s, 1H), 2.33 (s, 3H, CH3), 2.10
1
1
29
13
(
s, 3H, CH3), 5.21 (s, J( H- Si) = 195.4 Hz, 2H) ppm.
C
14. Rofouei, M. K.; Lawless, G. A.; Morsali, A.; Hitchcock, P. B. Inorg.
Chim. Acta. 2006, 359(12), 3815-3823.
NMR (75.5 M3Hz, C6D6): δ 144.3, 139.9, 137.0, 130.5, 126.2,
29
15. Schröck, R.; Angermaier, K.; Sladek, A.; Schmidbaur, H. J. Organomet.
Chem. 1996, 509, 85-88.
2
2.2 (CH3), 21.0 (CH3) ppm. Si NMR (59.64 MHz, C6D6): δ
+
−
40.4 ppm. MS (70 eV, m/z) = 240.1 (M ).
1
1
6. Bolte, M. Private Communication. 2010.
7. Blinka, T. A.; Helmer, B. J.; West, R. Advances in Organometallic Chem-
istry; Academic Press: San Diego, CA, 1984; pp. 193-218.
1
1
8. Grajewska, A.; Oestreich, M. Synlett. 2010, 2010(16), 2482-2484.
9. Prince, P. D.; Bearpark, M. J.; McGrady, G. S.; Steed, J. W. Dalton Trans.
-Anthracenyl SiH (10)
1
2.9 g 9-anthracenyl2SiCl2 (28.4 mmol, 1 equiv.) in 200 mL Et2O
2008(2), 271-282.
and 50 mL THF 1.18 g LiAlH4 pellets (31.3 mmol, 1.2 equiv.) in
20. Braddock-Wilking, J.; Schieser, M.; Brammer, L.; Huhmann, J.;
1
50 mL Et2O. 100 mL degassed H2SO4 (10%). Yields 83% (9.1 g,
Shaltout, R. J. Organomet. Chem. 1995, 499(1–2), 89-98.
2
1. Binder, J.; Fischer, R.; Flock, M.; Torvisco, A.; Uhlig, F. Phosphorus,
Sulfur Silicon Relat. Elem. 2015, 190(11), 1980-1993.
2. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem. Int. Ed.
2
3.7 mmol) of a brown-yellowish solid. Cold toluene was added
to the solid. Insoluble byproducts were removed by filtration,
followed by evaporation of the solvent and sublimation of the
obtained yellow powder, to remove anthracene. Recrystalliza-
tion in ethyl acetate yields 38.7% (4.23 g, 10.9 mmol) of pure
2
2003, 42(11), 1210-1250.
23. Bernal, J. D. Proc. R. Soc. London, Ser. A. 1924, 106, 749-773.
24. McL Mathieson, A.; Robertson, J. M.; Sinclair, V. C. Acta Cryst. 1950,
3(4), 245-250.
1
product in bright yellow needles. mp = 200–202°C. H NMR
2
5. Zeppek, C.; Pichler, J.; Torvisco, A.; Flock, M.; Uhlig, F. J. Organomet.
Chem. 2013, 740(0), 41-49.
(
300 MHz, C6D6): δ 8.79 (d, 4H), 8.22 (s, 2H), 7.73 (d, 4H),
1
1
29
7
.04–7.14 (m, 8H), 6.50 (s, J( H- Si) = 202.1 Hz, 2H) ppm.
2
6. Zeppek, C.; Fischer, R. C.; Torvisco, A.; Uhlig, F. Can. J. Chem. 2014,
92(6), 556-564.
13
C NMR (75.5 MHz, C6D6): δ 125.1, 126.7, 129.9, 131.5, 131.8,
1
38.1 ppm. 29Si NMR (59.64 MHz, C6D6): δ −61.4 ppm. MS
27. Binder, J.; Fischer, R. C.; Torvisco, A., Uhlig, F. in prep. 2014.
+
28. Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001,
(
70 eV, m/z) = 384.2 (M ).
3
4(11), 885-894.
2
3
9. Janiak, C. J. Chem. Soc., Dalton Trans. 2000, (21), 3885-3896.
0. Nayak, S. K.; Sathishkumar, R.; Row, T. N. G. Cryst. Growth Des. 2010,
1
2(10), 3112-3118.
2
3
7
,-Xylyl SiH (11)
3
1. Silaghi-Dumitrescu, L.; Haiduc, I.; Cea-Olivares, R.; Silaghi-
2.5 g 2,6-xylyl2SiCl2 (72.9 mmol, 1 equiv.) in 100 mL Et2O,
.32 g LiAlH4 pellets (87.9 mmol, 1.2 equiv.) in 150 mL Et2O.
0 mL degassed H2SO4 (10%). No recrystallization was needed.
Dumitrescu, I.; Escudié, J.; Couret, C. J. Organomet. Chem. 1997,
5
45–546, 1-8.
3
3
2. Cortial, G.; Le Goff, X.-F.; Bousquie, M.; Boisson, C.; Le Floch, P.; Nief,
F.; Thuilliez, J. New J. Chem. 2010, 34(10), 2290-2297.
3. Cretiu, G.; Silaghi-Dumitrescu, L.; Silaghi-Dumitrescu, I.; Escudié,
J.; Toscano, A.; Hernandez, S.; Cea-Olivares, R. J. Organomet. Chem.
Yield 67% (11.7 g, 48.8 mmol) of colorless, hexagonal shaped
1
crystals. mp = 51–52°C. H NMR (300 MHz, C6D6): δ 6.91 (t,
1
1
29
2
1
1
H), 6.71 (d, 4H), 5.08 (s, J( H- Si) = 196.5 Hz, 2H), 2.16 (s,
2002, 659(1–2), 95-101.
13
2H, CH3) ppm. C NMR (75.5 MHz, C6D6): δ 124.3, 127.5,
3
3
4. Bruker. APEX2 and SAINT; Bruker AXS Inc.: Madison, WI, 2012.
5. Blessing, R. Acta Crystallogr. Sect. A: Found. Crystallogr. 1995, 51(1),
33-38.
29
30.1, 145.0, 21.3 (CH3) ppm. Si NMR (59.64 MHz, C6D6): δ
−
+
62.2 ppm. MS (70 eV, m/z) = 296.1 (M ).