Y. A. Ibrahim et al. / Tetrahedron 59 (2003) 5425–5430
5429
1
3
4
1
.2 Hz, 1H); C NMR (CDCl ): d, 150.3, 148.3, 135.9,
3
J¼8.1, 1.2 Hz, 1H), 8.22 (d, J¼8.2 Hz, 1H), 8.08 (d,
1
3
29.4, 129.3, 128.2, 127.7, 126.4, 121.0.
J¼8 Hz, 1H), 7.72 (m, 2H), 7.62 (m, 2H); C NMR
(CDCl ): d, 153.4, 144.3, 132.3, 130.8, 130.0, 128.5, 127.3,
126.9, 126.2, 123.9, 122.1, 121.7.
3
þ
1
3
(
.2.2. Isoquinoline. MS: m/z¼129 (M ); H NMR
CDCl ): d, 9.16 (s, 1H), 8.44 (d, J¼5.7 Hz, 1H), 7.79 (d,
3
þ
1
J¼5.6 Hz, 1H), 7.66 (d, J¼8.1 Hz, 1H), 7.55 (dt, J¼5.6,
3.2.14. Fluorenone. MS: m/z¼180 (M ); H NMR
13
1
1
1
.1 Hz, 1H), 7.53 (d, J¼6 Hz, 1H), 7.45 (dt, J¼8.1, 1.1 Hz,
(CDCl ): d, 7.63 (d, J¼7.6 Hz, 2H), 7.43 (m, 4H), 7.25
3
1
3
H); C NMR (CDCl ): d, 152.4, 142.9, 135.6, 130.2,
3
(m, 2H); C NMR (CDCl ): d, 193.7, 144.3, 134.6, 134.0,
128.9, 124.1, 120.2.
3
28.6, 127.5, 127.1, 126.3, 120.3.
þ
1
3
7
.2.3. Indene. MS: m/z¼116 (M ); H NMR (CDCl ): d,
3
.45 (d, J¼7.2 Hz, 1H), 7.34 (d, J¼7.6 Hz), 7.25 (t, 1H,
Acknowledgements
J¼7.2 Hz), 7.15 (dt, 1H, J¼0.6, 7.2 Hz), 6.85 (m, 1H), 6.50
1
3
(
m, 1H), 3.35 (s, 2H); C NMR (CDCl ): d, 144.7, 143.5,
3
The support of the University of Kuwait received through
research grant no. SC06/01 and the facilities of ANALAB
and SAF (grants no. GS01/01, GS02/01, GS03/01) are
gratefully acknowledged. Also, the valuable discussions and
suggestions of Dr R. A. Aitken (University of St Andrews)
regarding the intermediates and mechanism of these FVP
reactions are highly appreciated.
1
34.0, 132.0, 126.1, 124.4, 123.6, 120.9, 39.0.
þ
1
3
.2.4. 2-Naphthol. MS: m/z¼144 (M ); H NMR (CDCl þ
3
DMSO-d ): d, 9.5 (s, 1H), 7.68 (m, 3H), 7.33 (t, J¼7.5 Hz,
6
1
3
1
H), 7.20 (t, J¼7.5 Hz, 1H), 7.11 (m, 2H); C NMR
3
(
CDCl ): d, 155.3, 134.6, 129.0, 127.8, 127.4, 125.8 (2C),
22.4, 118.5, 108.7.
1
þ
1
3
.2.5. 1-Naphthol. MS: m/z¼144 (M ); H NMR (CDCl ):
3
d, 8.15 (m, 1H), 7.78 (m, 1H), 7.45 (m, 3H), 7.25 (t, J¼8 Hz,
References
1
3
1
1
1
H), 6.72 (d, J¼7 Hz, 1H); C NMR (CDCl ): d, 151.2,
3
34.7, 127.6, 126.4, 125.8, 125.2, 124.3, 121.4, 120.7,
08.7.
1. (a) Smalley, R. K. Comprehensive Heterocyclic Chemistry;
Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984;
Vol. 7, p 491, and references cited therein. (b) Le Count, D. J.
Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.,
Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996;
Vol. 9, pp 37–39, and references cited therein.
þ
1
3
3
7
1
.2.6. Aniline. MS: m/z¼93 (M ); H NMR (CDCl ): d,
3
.67 (s, 2H), 6.75 (d, J¼7.6 Hz, 2H), 6.86 (t, J¼7.6 Hz, 1H),
1
3
.25 (t, J¼7.6 Hz, 2H); C NMR (CDCl ): d, 146.4, 129.2,
3
18.4, 115.0.
2. Smith, P. A. S. In Azides and Nitrenes; Scriven, E. V., Ed.;
Academic: New York, 1984; p 259.
þ
.31 (s); C NMR (CDCl ): d, 128.3.
1
3
7
.2.7. Benzene. MS: m/z¼78 (M ); H NMR (CDCl ): d,
3. Yunger, C. G.; Bell, R. A. J. Chem. Soc., Chem. Commun.
1992, 1359.
3
1
3
3
4
. (a) Leyva, E.; Yung, M. J. T.; Platz, M. S. J. Am. Chem. Soc.
1986, 108, 8307–8309, and references cited therein. (b)
Abramovitch, R. A.; Chelland, S. R.; Scriven, E. F. V. J. Org.
Chem. 1972, 37, 2705–2710. (c) Abramovitch, R. A.; Chel-
land, S. R.; Scriven, E. F. V. J. Am. Chem. Soc. 1972, 94,
1374–1376. (d) Sundberg, R. T.; Suter, S. R.; Brenner, M.
J. Am. Chem. Soc. 1972, 94, 513–520.
þ
3
.2.8. Naphtho[2,1-d][1,3]oxazole 18. MS: m/z¼169 (M );
1
H NMR (CDCl ): d, 8.51 (d, J¼8 Hz, 1H), 8.19 (s, 1H),
3
7
.92 (d, J¼8.2 Hz, 1H), 7.77 (d, J¼9 Hz, 1H), 7.65 (m, 2H),
1
3
7
1
1
.52 (t, J¼7 Hz, 1H); C NMR (CDCl ): d, 151.5, 147.4,
3
35.4, 131.1, 128.5, 127.2, 126.6, 126.5, 125.4, 122.0,
10.9.
5
. Dunkin, I. R.; El Ayeb, A. A.; Gallivan, S. L.; Lynch, M. A.
J. Chem. Soc., Perkin Trans. 2 1997, 1419–1427, and
references cited therein.
þ
CDCl ): d, 10.19 (s, 1H), 8.27 (s, 1H), 7.98–7.81 (m, 4H),
1
3
(
.2.9. 2-Naphthaldehyde. MS: m/z¼156 (M ); H NMR
3
1
3
7
.65–7.65 (m, 2H); C NMR (CDCl ): d, 192.0, 136.4,
3
6. (a) Ibrahim, Y. A.; Kaul, K.; Al-Awadi, N. A. Tetrahedron
2001, 57, 10171–10176. (b) Kumar, A.; Al-Awadi, N. A.;
Elnagdi, M. H.; Ibrahim, Y. A.; Kaul, K. Int. J. Chem. Kinet.
2001, 33, 402–406.
1
34.3, 134.1, 132.6, 129.4, 129.0 (2C), 128.0, 127.0, 122.7.
þ
.61 (m, 2H), 7.63 (m, 1H), 7.25 (m, 2H); C NMR
1
3
8
.2.10. Pyridine. MS: m/z¼89 (M ); H NMR (CDCl ): d,
3
1
3
7. (a) Moody, C. J. Org. React. Mech. 1985, 223–243. (b)
Aitken, R. A. Org. React. Mech. 1986, 227–245. (c) Aitken,
R. A. Org. React. Mech. 1987, 247–269.
(
CDCl ): d, 149.8, 135.8, 123.6.
3
þ
.22 (t, 2H), 6.91 (t, 1H), 6.81 (d, 2H), 5.7 (br, 1H);
1
3
.2.11. Phenol. MS: m/z¼94 (M ); H NMR (CDCl ): d,
8. Patterson, J. M.; Issidorides, C. H.; Papadopoulos, E. P.;
Smith, W. T. Tetrahedron Lett. 1970, 11, 1247–1250.
9. Katritzky, A. R.; Rachwal, B.; Rachwal, S. J. Heterocycl.
Chem. 1993, 30, 135–139.
3
1
3
7
NMR (CDCl ): d, 155.2, 129.7, 120.9, 115.4.
C
3
þ
1
3
(
.2.12. p-Aminophenol. MS: m/z¼109 (M ); H NMR
10. Aitken, R. A.; Drysdale, M. J.; Ferguson, G.; Lough, A. J.
J. Chem. Soc., Perkin Trans. 1 1998, 875–880.
11. Ibrahim, Y. A.; Al-Awadi, N. A.; Kaul, K. Tetrahedron 2001,
57, 7377–7381.
CDCl ): d, 3.67 (s, 2H), 6.42 (d, J¼7.6 Hz, 2H), 6.46 (d,
3
1
3
J¼7.6 Hz, 2H); C NMR (CDCl ): d, 148.1, 140.4, 115.4,
3
1
15.2.
1
2. Vogel Text Book of Practical Organic Chemistry; 5th ed.
Furniss, B. S., Hannaford, A. J., Smith, P. W. G., Tatchell,
A. R., Eds.; Wiley: New York, 1989; p 948 see also p 979.
þ
1
3
(
.2.13. Phenanthridine. MS: m/z¼179 (M ); H NMR
CDCl ): d, 9.32 (s, 1H), 8.65 (d, J¼8.3 Hz, 1H), 8.61 (dd,
3