3156
E. Artuso et al. / Tetrahedron 62 (2006) 3146–3157
2
7
4
1
-chlorobenzenediazonium tetrafluoroborate (0.34 g,
.5 mmol) and was complete after 10 min at rt. After the
31–36. (d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.;
Matsuda, T. J. Org. Chem. 1981, 46, 4885–4888.
usual work up, the crude residue was column chromato-
graphed, eluting with PE/Et O, 9.5:0.5, to afford a mixture
5. For example, see: (a) Brunner, H.; Le Cousturier de
Courcy, N.; Genet, J.-P. Tetrahedron Lett. 1999, 40,
4815–4818 and references cited therein. (b) Colas, C.;
Goeldner, M. Eur. J. Org. Chem. 1999, 1357–1366. (c)
Desmazeau, P.; Legros, J.-Y.; Fiaud, J.-C. Tetrahedron Lett.
1998, 39, 6707–6710 and references cited therein. (d)
Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S.; Guha, J.
2
(0.19 g, 73% yield) of the title compound 12f and the
regioisomer 3-(4-chlorophenyl)cyclopentene, in a 86:14 GC
1
ratio; H NMR (CDCl , 200 MHz): d 1.55–1.70 (m, 1H),
3
1
2
5
7
.89–2.03 (apparent quintet, 2H), 2.30–2.41 (m, 3H),
.41–2.52 (m, 2H), 2.56–2.67 (m, 2H), 3.73–3.88 (m, 1H),
.67–5.71 (m, 1H), 5.89–5.92 (m, 1H), 6.11 (m, 1H),
.06 (d, JZ8.8 Hz, 2H), 7.20 (d, JZ8.8 Hz, 2H), 7.21
J. Chem. Soc., Perkin Trans. 1 1998, 407–410 and
references cited therein. (e) Sengupta, S.; Bhattacharyya,
(
d, JZ8.6 Hz, 2H), 7.28 (d, JZ8.6 Hz, 2H).
S.; Sadhukhan, S. K. J. Chem. Soc., Perkin Trans. 1 1998,
2
75–277 and references cited therein. (f) Sengupta, S.;
Sadhukhan, S. K. Tetrahedron Lett. 1998, 39, 715–718 and
references cited therein. (g) Sengupta, S.; Sadhukhan, S. K.;
Bhattacharyya, S. Tetrahedron 1997, 53, 2213–2218 and
references cited therein. (h) Beller, M.; Kuhlein, K.
Synlett 1995, 441–442 and references cited therein. (i)
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Commun. 1995, 25, 651–657. (j) Sengupta, S.; Bhattacharya, S.
J. Chem. Soc., Perkin Trans. 1 1993, 1943–1944.
4.8.6. 1-(4-Nitrophenyl)cyclopentene (12i). The reaction
was carried out as described above, starting from
2
7
4
1
-nitrobenzenediazonium tetrafluoroborate
.5 mmol) and was complete after 10 min at rt. After the
(0.36 g,
usual work up, the crude residue was column chromato-
graphed, eluting with PE/Et O, 9:1, to afford a mixture
2
(0.24 g, 84% yield) of the title compound 12i and the
regioisomer 3-(4-nitrophenyl)cyclopentene, in a 79:21 GC
1
ratio; H NMR (CDCl , 200 MHz): d 1.67–1.83 (m, 1H),
6. For recent examples, see: (a) Dai, M.; Liang, B.; Wang, C.;
Chen, J.; Yang, Z. Org. Lett. 2004, 6, 221–224. (b) Masllorens,
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Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4,
3
1
2
5
7
.99–2.14 (apparent quintet, 2H), 2.46–2.54 (m, 3H),
.56–2.60 (m, 2H), 2.70–2.78 (m, 2H), 3.98–4.02 (m, 1H),
.74–5.79 (m, 1H), 6.02–6.06 (m, 1H), 6.42 (m, 1H),
.34 (d, JZ8.8 Hz, 2H), 7.54 (d, JZ8.3 Hz, 2H), 8.15 (d,
JZ8.8 Hz, 2H), 8.16 (d, JZ8.3 Hz, 2H).
2
079–2082. (e) Lange, W.; Komoschinski, J.; Eckert, M.;
Dockner, M. US 2002/0115885 (Bayer Corporation); Chem.
Abstr. 2002, 137, 169320. (f) Carpes, M. J. S.; Correia,
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Huaxue Tongbao 2002, 65, WO48/1-WO48/4; Chem. Abstr.
2002, 137, 278954. (h) Darses, S.; Pucheault, M.; Genet, J.-P.
Eur. J. Org. Chem. 2001, 1121–1128.
Acknowledgements
This work was supported by Italian MIUR, National Project
Dry-state Arenediazonium o-Benzenedisulfonimides: Syn-
thesis, Reactivity and Applications’ and by University of
Torino.
‘
7. (a) Isacoff, H. In Kirk-Othmer, Encyclopedia of Chemical
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1
986, pp 99–101.
8
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2
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