Andreas Ehrentraut, et al.
FULL PAPERS
2
115.7 (d, JC,F 22.0 Hz), 44.7; 19F NMR (235.4 MHz, CDCl3,
1707, 806 cmÀ1; anal. calcd. for C13H16O: C 82.94, H 8.57%;
found: C 82.84, H 8.27%.
297 K): d À 116.2; MS (E.I., 70 eV): m/z 308 (M ), 203, 201,
105; IR (KBr): n 1683, 1489, 1456, 1448, 1235, 1223, 1209, 757,
687 cmÀ1; anal. calcd. for C20H14F2O: C 77.91, H 4.58%; found:
C 77.95, H 4.82%.
Acknowledgements
The authors thank Dr. C. Fischer and Mrs. S. Buchholz (IfOK)
for analytical support. Generous support from Degussa AG
(former Aventis R&T) and the Deutsche Forschungsgemein-
schaft are gratefully acknowledged.
a-(4-Methoxyphenyl)-a-phenylacetophenone
1H NMR (400.1 MHz, CDCl3, 297 K): d 7.94 7.88 (m, 2H),
7.45 7.08 (m, 10H), 6.80 6.75 (m, 2H), 5.91 (s, 1H), 3.68 (s,
3H); 13C{1H} NMR (100.6 MHz, CDCl3, 297 K): d 198.9,
159.1, 139.9, 137.3, 133.4, 131.6, 130.6, 129.5, 129.4, 129.1, 129.0,
127.5, 114.6, 59.0, 55.7; MS (E.I., 70 eV): m/z 302 (M ), 197,
References and Notes
153, 105; IR (KBr): n 1688, 1513, 1446, 1278, 1256, 1207, 1182,
1025, 808, 697, 598 cmÀ1; anal. calcd. for C21H18O2: C 83.42, H
6.00%; found: C 83.36, H 6.28%.
≤Deceased September 28, 2001.
[1] M. Beller, A. Zapf, W. M‰gerlein, Chem. Eng. Techn.
2001, 24, 575.
[2] a) W. A. Herrmann, C. Bro˚mer, K. ÷fele, T. Priermeier,
M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989;
Angew. Chem. Int. Ed. 1995, 34, 1844; b) M. Beller, H.
Fischer, W. A. Herrmann, C. Bro˚mer, Angew. Chem.
1995, 107, 1992; Angew. Chem. Int. Ed. 1995, 34, 1848;
c) M. Beller, T. H. Riermeier, S. Haber, H.-J. Kleiner,
W. A. Herrmann, Chem. Ber. 1996, 129, 1259; d) M.
Beller, T. H. Riermeier, Tetrahedron Lett. 1996, 37, 6535;
e) W. A. Herrmann, C. Bro˚mer, C.-P. Reisinger, K.
÷fele, M. Beller, T. H. Riermeier, Chem. Eur. J. 1997, 3,
1357; f) M. Beller, T. H. Riermeier, C.-P. Reisinger,
W. A. Herrmann, Tetrahedron Lett. 1997, 38, 2073;
g) M. Beller, T. H. Riermeier, Eur. J. Inorg. Chem.
1998, 29; h) M. Beller, T. H. Riermeier, W. M‰gerlein,
T. E. M¸ller, W. Scherer, Polyhedron 1998, 17, 1165; i) G.
Stark, T. H. Riermeier, M. Beller, Synth. Commun. 2000,
30, 1703; j) A. Zapf, M. Beller, Chem. Eur. J. 2001, 7,
2908.
a-(2-Fluorophenyl)-a-phenylacetophenone
1H NMR (400.1 MHz, CDCl3, 297 K): d 8.35 8.25 (m, 2H),
7.82 7.30 (m, 12H), 6.62 (s, 1H); 13C{1H} NMR (100.6 MHz,
CDCl3, 297 K): d 197.7, 160.6 (d, 1JC,F 246 Hz), 137.6, 136.8,
133.6, 131.1 (d, 2JC,F 2.9 Hz), 129.9, 129.4, 129.4, 129.3, 129.1,
127.9, 127.2 (d, 3JC,F 14.3 Hz), 124.6 (d, 3JC,F 3.8 Hz), 115.7
(d, 2JC,F 22.0 Hz), 52.4; 19F NMR (235.4 MHz, CDCl3, 297 K):
d À 116.5; MS (E.I., 70 eV): m/z 290 (M ), 105; IR (KBr):
n 1683, 1486, 1452, 1225, 757, 742, 701 cmÀ1; anal. calcd. for
C20H15FO: C 82.74, H 5.21%; found: C 82.68, H 5.46%.
2-(4-Methylphenyl)indan-1-one
1H NMR (400.1 MHz, CDCl3, 297 K): d 8.80 8.00 (m, 8H),
3
3
3
4.83 (dd, JH,H 4.1 Hz, JH,H 8.2 Hz, 1H), 4.64 (dd, JH,H
2
3
2
8.3 Hz, JH,H 17.2 Hz, 1H), 4.22 (dd, JH,H 3.9 Hz, JH,H
17.2 Hz, 1H), 3.29 (s, 3H); 13C{1H} NMR (100.6 MHz, CDCl3,
297 K): d 206.1, 154.1, 137.1, 136.7, 135.4, 130.0, 128.1, 126.9,
126.8, 125.6, 124.9, 53.5, 36.3, 21.5; MS (E.I., 70 eV): m/z 222
¬
[3] Recent examples: a) M. Gomez Andreu, A. Zapf, M.
Beller, Chem. Commun. 2000, 2475; b) W. M‰gerlein, A.
Indolese, M. Beller, Angew. Chem. 2001, 113, 2940;
Angew. Chem. Int. Ed. 2001, 40, 2856; b) W. M‰gerlein,
A. Indolese, M. Beller, J. Organomet. Chem. 2002, 641,
30.
(M ), 207, 193, 178; IR (KBr): n 1681, 1448, 1204, 791, 756,
737, 698, 684, 604 cmÀ1; HRMS calcd. for C16H14O: 222.10446;
found: 222.10539.
[4] Selected examples: a) A. F. Littke, G. C. Fu, Angew.
Chem. 1998, 110, 3586; Angew. Chem. Int. Ed. 1998, 37,
3387; b) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am.
Chem. Soc. 1998, 120, 9722; c) J. P. Wolfe, S. L. Buch-
wald, Angew. Chem. 1999, 111, 2570; Angew. Chem. Int.
Ed. 1999, 38, 2413; d) J. P. Wolfe, R. A. Singer, B. H.
Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550;
e) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J.
Org. Chem. 1999, 64, 6797; f) A. F. Littke, G. C. Fu, J.
Org. Chem. 1999, 64, 10; g) K. H. Shaughnessy, P. Kim,
J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123; h) J. F.
Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy,
L. M. Alcazar-Roman, J. Org. Chem. 1999, 64, 5575; i) X.
Bei, T. Uno, J. Norris, H. W. Turner, W. H. Weinberg,
A. S. Guram, Organometallics 1999, 18, 1840; j) X. Bei,
T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W.
Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999,
2,2-Bis(4-methylphenyl)indan-1-one
1H NMR (400.1 MHz, CDCl3, 297 K): d 7.75 6.98 (m, 12H),
3.81 (s, 2H), 2.22 (s, 6H); 13C{1H} NMR (100.6 MHz, CDCl3,
297 K): d 206.1, 152.5, 141.0, 136.7, 136.2, 135.6, 129.5, 128.5,
128.3, 126.3, 125.5, 62.6, 45.3, 21.4; MS (E.I., 70 eV): m/z 312
(M ), 297, 252, 220, 178, 126, 57; IR (KBr): n 1707, 1603, 1511,
815, 768 cmÀ1.
a-(4-Methylphenyl)cyclohexanone
1H NMR (400.1 MHz, CDCl3, 297 K): d 7.12 7.04 (m, 2H),
7.00 6.92 (m, 2H), 3.53 3.48 (m, 1H), 2.50 1.40 (m, 8H), 2.26
(s, 3H); 13C{1H} NMR (100.6 MHz, CDCl3, 297 K): d 211.0,
136.9, 136.1, 129.5, 128.8, 57.4, 42.6, 35.5, 28.3, 25.8, 21.5; MS
(E.I., 70 eV): m/z 188 (M ), 144, 91; IR (KBr): n 2937, 2859,
216
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