932
A. Alam et al. / Tetrahedron 63 (2007) 927–933
1
3
1
H, ArH); C NMR (101 MHz, CDCl ) d 143.2, 141.5,
3
Acknowledgements
1
(
35.5, 134.0, 131.4, 130.8, 128.5, 128.4, 128.2, 127.8; IR
KBr) 1574, 1491, 1301, 1247, 815, 740 cm ; EIMS
ꢁ
1
This work was supported by a Grant-in-Aid for Scientific
Research on Priority Areas (No. 16033205 and No.
1550023 ‘Reaction Control of Dynamic Complexes’) from
the Ministry of Education, Culture, Sports, Science, and
Technology, Japan. We are also grateful to S. Nakajo (Divi-
sion of Elemental Analysis, Iwate university) for elemental
analyses.
+
(70 eV) m/z 286 (M ); Anal. Calcd for C H S : C, 41.93;
1
H, 2.11. Found: C, 42.18; H, 2.07.
0 6 5
4
.1.5. 1,8-Naphthalenedithiol (8). For isolation of 1,8-
naphthalenedithiol, the generated lithium intermediates were
thiated with elemental sulfur, reduced with LiAlH , and
4
refluxed in THF for 6 h. The reduced mixture was quenched,
acidified, and extracted with CH Cl . Recrystallization of
crude product from the same solvent, gave product 8 in
2
2
References and notes
1
2
6
2% yield as bright yellow crystal.
1
. (a) Sato, R.; Akutsu, Y.; Goto, T.; Saito, M. Chem. Lett. 1987,
2161; (b) Sato, R.; Onodera, A.; Goto, T.; Saito, M. Chem. Lett.
1989, 2111; (c) Sato, R.; Ogawa, S.; Saito, M. Chem. Lett.
1
H NMR (400 MHz, CDCl ) d 4.13 (s, 2H, ArH), 7.23 (t, 2H,
3
ArH), 7.87(d, J¼7.3 Hz, 2H, ArH), 7.81(d, J¼7.3 Hz, 2H, ArH).
1
990, 139.
4.1.6. 1,8-Naphthalenedisulfide (9). Compound 8 was
treated with S /NH in dilute solution of CH Cl and product
2. (a) Konstantinova, L. S.; Rakitin, O. A.; Rees, C. W. Chem. Rev.
2004, 104, 2617; (b) Chartterji, T.; Gates, K. S. Bioorg. Med.
Chem. Lett. 1998, 8, 535.
8
3
2
2
1
3
9
was isolated quatitatively.
3
. (a) Beher, V.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115,
7017; (b) Ford, P. W.; Davidson, B. S. J. Org. Chem. 1993, 58,
4522; (c) Toste, F. D.; Still, I. W. J. J. Am. Chem. Soc. 1995,
117, 7261; (d) Ford, P. W.; Narbut, M. R.; Belli, J.;
Davidson, B. S. J. Org. Chem. 1994, 59, 5955.
4
.1.7. 2,2-Dimethylphenanthro[9,10-d][1,3,2]dithiastan-
nole (12). The synthetic procedure was as same as that of
compound 2 or 6. The compound was isolated only in 4%
yield because of the extensive lithiation of the peri position
as same as 1-napthalenethiol.
4. (a) Bergman, J.; Stalhansky, C. Tetrahedron Lett. 1994, 35,
279; (b) Rewcastle, G. W.; Janosik, T.; Bergman, J.
Tetrahedron 2001, 51, 7185.
5. Tomas, J.; Birgitaa, S.; Bergman, J. J. Org. Chem. 2002, 67,
6220.
6. Gingras, M.; Raimundo, J.-M.; Chabre, Y. M. Angew. Chem.,
Int. Ed. 2006, 45, 1686.
7. Ogawa, S.; Nobuta, S.; Nakayama, R.; Kawai, Y.; Niizuma, S.;
Sato, R. Chem. Lett. 1996, 757.
8. (a) Feher, F.; Langer, M. Tetrahedron Lett. 1971, 2125; (b)
Feher, F.; Langer, M.; Volkert, R. Z. Naturforsch., B: Chem.
Sci. 1972, 27, 1006; (c) Chenard, B. L.; Milller, T. J. J. Org.
Chem. 1984, 49, 1221; (d) Sato, R.; Saito, S.; Chiba, H.;
Goto, T.; Saito, M. Chem. Lett. 1986, 349; (e) Gronowitz, S.;
Moses, P.; Hornfeldt, A. Ark. Kemi 1960, 17, 237.
9. Chenard, B. L.; Harlow, R. L.; Johnson, A. L.; Vladuchick,
S. A. J. Am. Chem. Soc. 1985, 107, 3871.
5
ꢀ
1
Colorless crystal, mp 202.0–209.5 C (decomp.); H NMR
(
400 MHz, CDCl ) d 8.62 (dd, J¼8.0, 1.4 Hz, 2H, ArH),
3
8
1
6
1
1
.54 (dd, J¼8.0, 1.2 Hz, 2H, ArH), 7.63 (td, J¼8.0,
.4 Hz, 2H, ArH), 7.54 (td, J¼8.0 Hz, 2H, ArH), 1.08 (s,
1
3
H, Me); C NMR (101 MHz, CDCl ) d 134.1, 132.5,
3
29.0, 128.0, 127.0, 125.7, 122.7, 2.4; IR (KBr) 3066,
554, 1511, 1480, 1274, 1197, 882, 749, 714 cm ; EIMS
ꢁ
1
+
(
70 eV) m/z 390 (M ); Anal. Calcd for C H S Sn: C,
1
0 14 2
4
9.39; H, 3.63. Found: C, 49.19; H, 3.60.
4
.1.8. Phenanthro[9,10-f]pentathiepin (13). The synthetic
procedure was as same as that of product 3 or 7. Two prod-
ucts were isolated in 55 and 18% yield, respectively. After
complete identification, it was found that the two products
are phenanthrene having C S and C S rings, respectively.
2
7
2 3
Products were isolated by usual column chromatography
with n-hexane as an eluent. Compound 13 was found as
yellow crystal.
10. Sato, R.; Saito, S.; Chiba, H.; Goto, T.; Saito, M. Bull. Chem.
Soc. Jpn. 1988, 61, 1647.
11. Block, E.; Eswarakishnan, V.; Gernon, M.; Ofori-Okai, G.;
Saha, C.; Tang, K.; Zubieta, J. J. Am. Chem. Soc. 1989, 111,
658.
ꢀ
1
Mp 148.0 C; H NMR (400 MHz, CDCl ) d 7.73–7.79 (m,
3
4
H, ArH), 8.75 (dd, J¼6.4, 2.2 Hz, 2H, ArH), 7.81 (dd,
12. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn.
1988, 61, 953.
13. Zweig, A.; Hoffmann, A. K. J. Org. Chem. 1965, 30, 3997.
14. Stephen, M. A.; Heather, S. D.; Stuart, D. R.; Alexandra,
M. Z. S.; Woollins, J. D. Heteroat. Chem. 2004, 15, 530.
15. Pratap, R.; Castle, R. N.; Lee, M. L. J. Heterocycl. Chem. 1982,
1
3
J¼6.7, 2.3 Hz, 2H, ArH); C NMR (101 MHz, CDCl )
3
d 122.9, 127.9, 128.7, 129.6, 131.5, 132.3, 142.6; IR (KBr)
1
ꢁ
1
478, 1443, 1146, 757, 719 cm ; EIMS (70 eV) m/z 272
+
(M ꢁ2S); Anal. Calcd for C H S : C, 49.96; H, 2.40.
Found: C, 49.60; H, 2.56.
1
4 8 5
1
9, 439.
16. Faher, F.; Engelen, B. Z. Anorg. Allg. Chem. 1979, 452, 37.
7. Faher, F.; Lex, J. Z. Anorg. Allg. Chem. 1976, 423, 103.
4
.2. Crystallographic information
1
X-ray crystal data for compounds 3 and 13 have been depos-
ited in Cambridge Crystallographic Data Center as supple-
mentary publication number CCDC 626593 and CCDC
18. Steudel, R.; Steidel, J.; Pickardt, J.; Schuster, F. Z.
Naturforsch., B: Chem. Sci. 1980, 35B, 1378.
19. (a) Burshka, C.; Leonard, K.; Werner, H. Z. Anorg. Allg. Chem.
1980, 464, 30; (b) Muller, E. G.; Peterson, J. L.; Dahl, L. F.
J. Organomet. Chem. 1976, 111, 91.
6
26594, respectively. Copies of the data can be obtained,
free of charge, on application to CCDC, 12 Union Road,
20. Donohue, J.; Caron, A.; Goldish, E. J. Am. Chem. Soc. 1961,
83, 3748.