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M. Sonoda et al. / Tetrahedron Letters 43 (2002) 5269–5272
2. For thermal cycloaromatization of dienynes: (a) Schluz,
cm−1; UV umax (log m) 360 (sh, 3.80), 337 (4.47), 262 (4.41)
nm; MS (EI) m/z 230 (M+). Anal. calcd for C18H14: C,
93.87; H, 6.13. Found: C, 93.50; H, 6.05%. For 1b ((Z,
Z)-isomer): 1H NMR (300 MHz, CDCl3, 30°C) l 8.29
(dd, J=6.0, 1.5 Hz, 1H), 7.81–7.77 (m, 2H), 7.59 (dd,
J=6.0, 1.2 Hz, 1H), 7.29–7.19 (m, 4H), 7.13 (ddd, J=7.8,
7.5, 1.5 Hz, 1H), 6.99 (d, J=12.0 Hz, 1H), 6.65 (d,
J=12.0 Hz, 1H), 6.05 (dd, J=12.0, 3.0 Hz, 1H), 5.86 (dd,
J=12.0, 3.0 Hz, 1H); 13C NMR (75 MHz, CDCl3, 30°C)
l 139.0 (d), 137.3 (d), 136.3 (s), 135.9 (s), 132.8 (d), 129.7
(d), 129.6 (d), 128.6 (d), 128.5 (d), 128.3 (d), 127.2 (d),
124.1 (s), 109.9 (d), 107.2 (d), 94.5 (s), 93.3 (s); IR (neat)
3061, 3023, 2162, 1587, 1492, 1466, 1447, 1434, 1416,
1023, 771, 741, 690 cm−1; UV umax (log m) 333 (4.30), 263
(4.28), 254 (sh, 4.26) nm; MS (EI) m/z 310, 308 (M+), 229
(M+−Br), 228 (M+−HBr). HRMS (EI) calcd for
C18H13Br: 310.0182, 308.0201. Found: 310.0221,
308.0145.
K.; Hofmann, J.; Zimmermann, G. Eur. J. Org. Chem.
1999, 3407–3412; (b) Hofmann, J.; Zimmermann, G.;
Homann, K.-H. Liebigs Ann. 1995, 841–848; (c) Zimmer-
mann, G. Eur. J. Org. Chem. 2001, 457–471 and refer-
ences cited therein.
3. For photochemical cycloaromatization of dienynes: (a)
Tinnemans, A. H. A.; Laarhoven, W. H. J. Chem. Soc.,
Perkin Trans. 2 1976, 1111–1115; (b) Tinnemans, A. H.
A.; Laarhoven, W. H. J. Chem. Soc., Perkin Trans. 2
1976, 1115–1120; (c) Kaafarani, B. R.; Neckers, D. C.
Tetrahedron Lett. 2001, 42, 4099–4102.
4. (a) John, J. A.; Tour, J. M. J. Am. Chem. Soc. 1994, 116,
5011–5012; (b) John, J. A.; Tour, J. M. Tetrahedron 1997,
53, 15515–15534.
5. Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85–87.
6. (a) Chow, S.-Y.; Palmer, G. J.; Bowles, D. M.; Anthony,
J. E. Org. Lett. 2000, 2, 961–963; (b) Bowles, D. M.;
Palmer, G. J.; Landis, C. A.; Scott, J. L.; Anthony, J. E.
Tetrahedron 2001, 57, 3753–3760.
17. (E,E)-Isomer of 1a has been known: Hambrecht, J.;
Straub, H.; Mu¨ller, E. Chem. Ber. 1974, 107, 2985–2991.
18. The assignment of (E,Z)- and (E,E)-isomers was per-
formed on the basis of the symmetry and the coupling
constants between the vinyl protons in the 1H NMR
spectra. (E,Z)-isomer of 1a: l 7.00 (d, J=16.0 Hz, 1H),
6.67 (d, J=12.0 Hz, 1H), 6.42 (dd, J=16.0, 2.8 Hz, 1H),
5.89 (dd, J=12.0, 2.8 Hz, 1H). (E,E)-Isomer of 1a (the
non-first-order coupling constants were elucidated by
simulation): l 7.01–6.98 (m, J=16.1, 1.3, −0.5 Hz, 1H),
6.38–6.33 (m, J=16.1, 1.3, −0.5 Hz, 1H). One (E,Z)-iso-
mer of 1b: l 6.71 (d, J=11.7 Hz, 1H), 6.36 (dd, J=16.1,
2.7 Hz, 1H), 5.89 (dd, J=11.7, 2.7 Hz, 1H). The other
(E,Z)-isomer of 1b: l 6.94 (d, J=16.0 Hz, 1H), 6.34 (dd,
J=16.0, 2.8 Hz, 1H), 6.00 (dd, J=11.6, 2.8 Hz, 1H).
(E,E)-Isomer of 1b: l 7.02 (d, J=16.0 Hz, 1H), 6.36 (dd,
J=16.0, 2.4 Hz, 1H), 6.31 (dd, J=18.4, 2.4 Hz, 1H). The
vinyl proton signals of the isomers of 1b which appeared
at the lowest field were concealed by overlap with the
aromatic proton signals.
19. Irradiation of (E,E)-isomer of 1a in cyclohexane with a
high-pressure mercury lamp also resulted in E/Z isomer-
ization of the double bond; (E,E)-isomer:(E,Z)-iso-
mer:1a=47:46:8.
20. Bax, A.; Ferretti, J. A.; Nashed, N.; Jerina, D. M. J. Org.
Chem. 1985, 50, 3029–3034.
21. Yasuda, M.; Kojima, R.; Ohira, R.; Shiragami, T.;
Shima, K. Bull. Chem. Soc. Jpn. 1998, 71, 1655–1660.
22. Scott reported that flow pyrolysis of 5 at 1035°C (in a
stream of dry N2) did not give skeletal rearrangement
products but scrambling of the carbon atoms between
positions 5 and 6 took place in starting material 5: Scott,
L. T.; Tsang, T.-H.; Levy, L. A. Tetrahedron Lett. 1984,
25, 1661–1664.
7. Yamaguchi, S.; Swager, T. M. J. Am. Chem. Soc. 2001,
123, 12087–12088.
8. (a) Goldfinger, M. B.; Swager, T. M. J. Am. Chem. Soc.
1994, 116, 7895–7896; (b) Goldfinger, M. B.; Crawford,
K. B.; Swager, T. M. J. Org. Chem. 1998, 63, 1676–1686.
9. For a review: Mallory, F. B.; Mallory, C. W. Org. React.
1984, 30, 1–456. For the use of this reaction to construct
large phenacenes: (a) Mallory, F. B.; Butler, K. E.;
Evans, A. C.; Brondyke, E. J.; Mallory, C. W.; Yang, C.;
Ellenstein, A. J. Am. Chem. Soc. 1997, 119, 2119–2124;
(b) Mallory, F. B.; Butler, K. E.; Be´rube´, A.; Luzik, E.
D.; Mallory, C. W.; Brondyke, E. J.; Hiremath, P.; Ngo,
P.; Carroll, P. J. Tetrahedron 2001, 57, 3715–3724.
10. In contrast to the photochemical cycloaromatization,
thermal stilbene cyclization is much less common: Plater,
M. J. Tetrahedron Lett. 1994, 35, 801–802.
11. (a) Fonken, G. J. Chem. Ind. 1962, 1327; (b) Leznoff, C.
C.; Hayward, R. J. Can. J. Chem. 1972, 50, 528–533.
12. (a) Tobe, Y.; Nakagawa, N.; Naemura, K.; Waka-
bayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc.
1998, 120, 4544–4545; (b) Tobe, Y.; Nakagawa, N.;
Kishi, J.; Sonoda, M.; Naemura, K.; Wakabayashi, T.;
Shida, T.; Achiba, Y. Tetrahedron 2001, 57, 3629–3636.
See also: (c) Rubin, Y.; Parker, T. C.; Pastor, S. J.;
Jalistagi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int.
Ed. 1998, 37, 1226–1229; (d) Bunz, U. H. F.; Rubin, Y.;
Tobe, Y. Chem. Soc. Rev. 1999, 28, 107–119.
13. Frenklach, M.; Feigelson, E. D. Astrophys. J. 1989, 341,
372–384.
14. Glamb, V.; Alper, H. Tetrahedron Lett. 1983, 24, 2965–
2968.
15. Yasuike, S.; Shiratori, S.; Kurita, J.; Tsuchiya, T. Chem.
Pharm. Bull. 1999, 47, 1108–1114.
16. Selected data for 1a ((Z,Z)-isomer): mp 58–60°C; 1H
NMR (300 MHz, CDCl3, 30°C) (the non-first-order cou-
pling constants were elucidated by simulation) l 7.88–
7.85 (m, 4H), 7.35–7.27 (m, 6H), 6.69–6.64 (m, J=11.6,
1.6, −0.7 Hz, 2H), 5.96–5.91 (m, J=11.6, 1.6, −0.7 Hz,
2H); 13C NMR (75 MHz, CDCl3, 30°C) l 138.6 (s), 136.4
(d), 128.6 (d), 128.5 (d), 128.4 (d), 107.5 (d), 94.6 (s); IR
(KBr) 3059, 3025, 1595, 1491, 1449, 1417, 919, 789, 690
23. (a) Sarobe, M.; Jenneskens, L. W.; Wiersum, U. E.
Tetrahedron Lett. 1996, 37, 1121–1122; (b) Brooks, M.
A.; Scott, L. T. J. Am. Chem. Soc. 1999, 121, 5444–5449;
(c) Plater, M. J. Tetrahedron Lett. 1994, 35, 6147–6150.
24. Necula and Scott reported that PAH 6 isomerized to
chrysene under flow pyrolysis condition at 1100°C in a
stream of dry N2: Necula, A.; Scott, L. T. J. Anal. Appl.
Pyrolysis 2000, 54, 65–87.