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5. Emsley, J. The Elements, 3rd ed.; Oxford Univerity Press:
Oxford, 1998.
6. Klein, R. F. X.; Svoronos, P. D. N.; Horak, V.; Jameson,
G. B.; Koritsa´nszky, T.; Ka´lma´n, A. J. Org. Chem. 1991,
56, 3259–3263 and references cited therein.
2. (a) Yoshimura, T. Rev. Heteroat. Chem. 2000, 22, 101–
120 and references cited therein; (b) Yoshimura, T.;
Takata, E.; Miyake, T.; Shimasaki, C.; Hasegawa, K.;
Tsukurimichi, E. Chem. Lett. 1992, 2213–2216; (c)
Yoshimura, T.; Hamada, K.; Imado, M.; Hamata, K.;
Tomoda, K.; Fujii, T.; Morita, H.; Shimasaki, C.; Ono,
S.; Tsukurimichi, E.; Furukawa, N.; Kimura, T. J. Org.
Chem. 1997, 62, 3802–3803; (d) Yoshimura, T.; Ohkubo,
M.; Fujii, T.; Kita, H.; Wakai, Y.; Ono, S.; Morita, H.;
Shimasaki, C.; Horn, E. Bull. Chem. Soc. Jpn. 1998, 71,
1629–1637; (e) Horn, E.; Dong, T.; Fujii, T.; Yoshimura,
T.; Shimasaki, C. Z. Kristallogr. NCS 2000, 215, 356–
357; (f) Yoshimura, T.; Fujii, T.; Murotani, S.; Miyoshi,
S.; Fujimori, T.; Ohkubo, M.; Ono, S.; Morita, H. J.
Organomet. Chem. 2000, 611, 272–279.
3. The side-products were mainly biphenyl (20%), diben-
zothiophen (6%), and triphenyl-l6-sulfanenitrile (7%),
The pheyl-l6-sulfanenitrile should be formed by the reac-
tion of 1 with the phenyl anion generated from ligand
exchange reaction.2c A complex reaction mixture includ-
ing some unidentified products was also obtained. For 2:
mp 198–200°C (dec.); 1H NMR (400 MHz, CDCl3): l
7.39 (t, J=6.6 Hz, 2H), 7.47 (t, J=6.6 Hz, 1H), 7.50 (t,
J=8.0 Hz, 2H), 7.65 (t, J=8.0 Hz, 2H), 7.66 (d, J=6.6
Hz, 2H), 7.78 (d, J=8.0 Hz, 2H), 7.89 (d, J=8.0 Hz,
2H); 13C NMR (100 MHz, CDCl3): l 121.5, 124.1, 125.2,
129.1, 130.8, 132.0, 133.4, 133.6, 144.7, 145.3; IR (KBr)
1261 cm−1 (SN); MS (m/z) 275 (M+). Calcd for
C18H13NS: C, 78.51; H, 4.76; N, 5.09. Found: C, 78.41;
H, 5.02; N, 5.12.
7. NBO version 3.1; Glendeling, E. D.; Reed, A. E.; Car-
penter, J. E.; Weinhold, F.
8. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev.
1988, 88, 899–926 and references cited therein; (b) Reed,
A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736–1740.
9. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M.
W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.;
Keith, T. A.; Petersson, G. A.; Montgomery, J. A.;
Raghavachari, K.; Al-Laham, M. A.; Zakrzewshi, V. G.;
Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B.
B.; Nanayakkara, A.; Challacomb, M.; Peng, C. Y.;
Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.;
Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.;
Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.;
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94, Revision E. 2, Gaussian, Inc.: Pittsburgh, PA, 1995.
10. Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990,
112, 1434–1445 and references cited therein.
11. For 3: mp 239–241°C; 1H NMR (400 MHz, CDCl3): l
7.59 (t, J=7.6 Hz, 2H), 7.64 (t, J=8.0 Hz, 2H), 7.72 (t,
J=7.6 Hz, 1H), 7.85 (t, J=8.0 Hz, 2H), 7.86 (d, J=7.6
Hz, 2H), 8.15 (d, J=8.0 Hz, 2H), 8.20 (d, J=8.0 Hz,
2H); 13C NMR (100 MHz, CDCl3): l 123.72, 127.05,
127.09, 130.66, 132.11, 132.67, 135.26, 135.49, 135.55,
137.09; IR (KBr) 1072 cm−1 (SN); FAB (m/z) 276 (M+−
Cl−). Calcd for C18H14ClNS: C, 69.33; H, 4.53; N, 4.49.
Found: C, 69.11; H, 4.64; N, 4.40.
4. Crystal data of 2: C18H17NO2S, M=311.40, monoclinic,
12. Crystal data of 3: C18H16ClNS, M=311.83, triclinic,
,
a=20.686(2), b=13.563(1), c=16.234(2) A, i=
,
a=10.125(1), b=10.655(1), c=8.3269(9) A, h=
3
,
136.246(4)°, U=3149.9(7) A , T=296 K, space group
111.777(7), i=101.727(9), k=91.309(9)°, U=812.0(2)
C2/c (no. 15), Z=8, v(Mo Ka)=2.12 cm−1, 4711 reflec-
tions measured, 4597 unique (Rint=0.015). The final R
value was 0.044. Crystallographic data for the structural
analysis has been deposited with the Cambridge Crystal-
lographic Data Centre, CCDC No. 162038 for compound
2.
3
,
(
A , T=296 K, space group P1 (no. 2), Z=2, v(Mo
Ka)=3.56 cm−1, 4982 reflections measured, 4978 unique
(Rint=0.018). The final R value was 0.049. Crystallo-
graphic data for the structural analysis has been
deposited with the Cambridge Crystallographic Data
Centre, CCDC No. 162039 for compound 3.
.