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Oligothiophenes: (a) Roncali, J. Acc. Chem. Res. 2000, 33, 147. (b) Fichou, D. J. Mater. Chem. 2000, 10, 571.
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Fichou, D.1
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Carbon-sulfur allotropic forms: (a) Lee, A. W. M.; Yeung, A. B. W.; Yuen, M. S. M.; Zhang, H.; Zhao, X.; Wong, W. Y. Chem. Commun. 2000, 75. (b) Frapper, G.; Saillard, J.-Y. J. Am. Chem. Soc. 2000, 122, 5367. (c) Genin, H.; Hoffmann, R. J. Am. Chem. Soc. 1995, 117, 12328. (d) Chou, J.-H.; Rauchfuss, T. B. Z. Naturforsch. B: Chem. Sci 1997, 52, 1549.
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Lee, A.W.M.1
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23
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Carbon-sulfur allotropic forms: (a) Lee, A. W. M.; Yeung, A. B. W.; Yuen, M. S. M.; Zhang, H.; Zhao, X.; Wong, W. Y. Chem. Commun. 2000, 75. (b) Frapper, G.; Saillard, J.-Y. J. Am. Chem. Soc. 2000, 122, 5367. (c) Genin, H.; Hoffmann, R. J. Am. Chem. Soc. 1995, 117, 12328. (d) Chou, J.-H.; Rauchfuss, T. B. Z. Naturforsch. B: Chem. Sci 1997, 52, 1549.
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24
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0000819511
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Carbon-sulfur allotropic forms: (a) Lee, A. W. M.; Yeung, A. B. W.; Yuen, M. S. M.; Zhang, H.; Zhao, X.; Wong, W. Y. Chem. Commun. 2000, 75. (b) Frapper, G.; Saillard, J.-Y. J. Am. Chem. Soc. 2000, 122, 5367. (c) Genin, H.; Hoffmann, R. J. Am. Chem. Soc. 1995, 117, 12328. (d) Chou, J.-H.; Rauchfuss, T. B. Z. Naturforsch. B: Chem. Sci 1997, 52, 1549.
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25
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Carbon-sulfur allotropic forms: (a) Lee, A. W. M.; Yeung, A. B. W.; Yuen, M. S. M.; Zhang, H.; Zhao, X.; Wong, W. Y. Chem. Commun. 2000, 75. (b) Frapper, G.; Saillard, J.-Y. J. Am. Chem. Soc. 2000, 122, 5367. (c) Genin, H.; Hoffmann, R. J. Am. Chem. Soc. 1995, 117, 12328. (d) Chou, J.-H.; Rauchfuss, T. B. Z. Naturforsch. B: Chem. Sci 1997, 52, 1549.
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Chou, J.-H.1
Rauchfuss, T.B.2
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27
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0035814415
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Thiophene-based helicenes: (a) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899. (b) Yamada, K.; Kobori, Y.; Nakagawa, H. Chem. Commun. 2000, 97. (c) Tanaka, K.; Osuga, H.; Suzuki, H.; Shogase, Y.; Kitahara, Y. J. Chem. Soc., Perkin Trans. 1 1998, 935. (d) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 61, 1151. (e) Yamada, K.; Ogashiwa, S.; Tanaka, H.; Nakagawa, H.; Kawazura, H. Org. Lett. 1981, 343. (f) Wynberg, H. Acc. Chem. Res. 1971, 4, 65.
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Phillips, K.E.S.1
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Jockusch, S.3
Lovinger, A.J.4
Turro, N.J.5
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28
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0034614345
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Thiophene-based helicenes: (a) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899. (b) Yamada, K.; Kobori, Y.; Nakagawa, H. Chem. Commun. 2000, 97. (c) Tanaka, K.; Osuga, H.; Suzuki, H.; Shogase, Y.; Kitahara, Y. J. Chem. Soc., Perkin Trans. 1 1998, 935. (d) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 61, 1151. (e) Yamada, K.; Ogashiwa, S.; Tanaka, H.; Nakagawa, H.; Kawazura, H. Org. Lett. 1981, 343. (f) Wynberg, H. Acc. Chem. Res. 1971, 4, 65.
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Yamada, K.1
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85042258656
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Thiophene-based helicenes: (a) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899. (b) Yamada, K.; Kobori, Y.; Nakagawa, H. Chem. Commun. 2000, 97. (c) Tanaka, K.; Osuga, H.; Suzuki, H.; Shogase, Y.; Kitahara, Y. J. Chem. Soc., Perkin Trans. 1 1998, 935. (d) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 61, 1151. (e) Yamada, K.; Ogashiwa, S.; Tanaka, H.; Nakagawa, H.; Kawazura, H. Org. Lett. 1981, 343. (f) Wynberg, H. Acc. Chem. Res. 1971, 4, 65.
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Tanaka, K.1
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Shogase, Y.4
Kitahara, Y.5
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30
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0001006849
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Thiophene-based helicenes: (a) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899. (b) Yamada, K.; Kobori, Y.; Nakagawa, H. Chem. Commun. 2000, 97. (c) Tanaka, K.; Osuga, H.; Suzuki, H.; Shogase, Y.; Kitahara, Y. J. Chem. Soc., Perkin Trans. 1 1998, 935. (d) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 61, 1151. (e) Yamada, K.; Ogashiwa, S.; Tanaka, H.; Nakagawa, H.; Kawazura, H. Org. Lett. 1981, 343. (f) Wynberg, H. Acc. Chem. Res. 1971, 4, 65.
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Larsen, J.1
Bechgaard, K.2
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31
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0346794754
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Thiophene-based helicenes: (a) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899. (b) Yamada, K.; Kobori, Y.; Nakagawa, H. Chem. Commun. 2000, 97. (c) Tanaka, K.; Osuga, H.; Suzuki, H.; Shogase, Y.; Kitahara, Y. J. Chem. Soc., Perkin Trans. 1 1998, 935. (d) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 61, 1151. (e) Yamada, K.; Ogashiwa, S.; Tanaka, H.; Nakagawa, H.; Kawazura, H. Org. Lett. 1981, 343. (f) Wynberg, H. Acc. Chem. Res. 1971, 4, 65.
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Org. Lett.
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Yamada, K.1
Ogashiwa, S.2
Tanaka, H.3
Nakagawa, H.4
Kawazura, H.5
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32
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33947293092
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Thiophene-based helicenes: (a) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899. (b) Yamada, K.; Kobori, Y.; Nakagawa, H. Chem. Commun. 2000, 97. (c) Tanaka, K.; Osuga, H.; Suzuki, H.; Shogase, Y.; Kitahara, Y. J. Chem. Soc., Perkin Trans. 1 1998, 935. (d) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 61, 1151. (e) Yamada, K.; Ogashiwa, S.; Tanaka, H.; Nakagawa, H.; Kawazura, H. Org. Lett. 1981, 343. (f) Wynberg, H. Acc. Chem. Res. 1971, 4, 65.
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(1971)
Acc. Chem. Res.
, vol.4
, pp. 65
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Wynberg, H.1
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33
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0034671517
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Rajca, A.; Wang, H.; Pink, M.; Rajca, S. Angew. Chem. Int. Ed. 2000, 39, 4481.
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(2000)
Angew. Chem. Int. Ed.
, vol.39
, pp. 4481
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Rajca, A.1
Wang, H.2
Pink, M.3
Rajca, S.4
-
34
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0142135375
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Determination of the absolute configuration of 1 by vibrational circular dichroism spectroscopy: Friedmann, T. B.; Cao, X.; Wang, H.; Rajca, A.; Nafie, L. A. J. Phys. Chem. A 2003, 107, 7692.
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(2003)
J. Phys. Chem. A
, vol.107
, pp. 7692
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Friedmann, T.B.1
Cao, X.2
Wang, H.3
Rajca, A.4
Nafie, L.A.5
-
35
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0028096576
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Synthesis of 4-bromo-2-octylthiophene 7 from propargyl bromide via acid-catalyzed cyclization of acetylenic ketones: Masquelin, T.; Obrecht, D. Tetrahedron Lett. 1994, 35, 9387.
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(1994)
Tetrahedron Lett.
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, pp. 9387
-
-
Masquelin, T.1
Obrecht, D.2
-
36
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0000763219
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3-Bromo-2-trimethylsilylthiophene may also be prepared in 87% yield from 2,3-dibromothiophene: Deffieux, D.; Bonafoux, D.; Bordeau, M.; Biran, C.; Dunogues, J. Organometallics 1996, 15, 2041.
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(1996)
Organometallics
, vol.15
, pp. 2041
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-
Deffieux, D.1
Bonafoux, D.2
Bordeau, M.3
Biran, C.4
Dunogues, J.5
-
38
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0346164220
-
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note
-
Attempts at direct alkylation of a-metallated 4 with 1-bromooctane resulted in either negligible extent of conversion and/or migration of the TMS group with alkylation at the a-position adjacent to the bromine.
-
-
-
-
40
-
-
84987246060
-
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t-BuOK-mediated alkylation: Brandsma, L.; Mal'kina, A. G.; Lochman, L.; von Schleyer, P. R. Recl. Trav. Chim. Pays-Bas 1994, 113, 529.
-
(1994)
Recl. Trav. Chim. Pays-Bas
, vol.113
, pp. 529
-
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Brandsma, L.1
Mal'kina, A.G.2
Lochman, L.3
Von Schleyer, P.R.4
-
41
-
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76949089512
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-
2-Octylthiophene may also be prepared by reaction of iodine with ate complexes of trioctylborane and 2-thienyllithium: Sotoyama, T.; Hara, S.; Suzuki, A. Bull. Chem. Soc. Jpn. 1979, 52, 1865.
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(1979)
Bull. Chem. Soc. Jpn.
, vol.52
, pp. 1865
-
-
Sotoyama, T.1
Hara, S.2
Suzuki, A.3
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42
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0033603636
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Bromination of 2-octylthiophene: Pabst, G. R.; Pfuller, O. C.; Sauer, J. Tetrahedron 1999, 55, 8045.
-
(1999)
Tetrahedron
, vol.55
, pp. 8045
-
-
Pabst, G.R.1
Pfuller, O.C.2
Sauer, J.3
-
45
-
-
0346794753
-
-
note
-
2O.
-
-
-
-
46
-
-
0348055742
-
-
note
-
1H resonance at δ = 7. 231 ppm appears as a broadened triplet (a singlet with two shoulders).
-
-
-
-
47
-
-
0346164221
-
-
note
-
1H NMR spectra of crude mixtures, are in the 40-50% range.
-
-
-
-
48
-
-
0346794751
-
-
note
-
(a) Allylic coupling of J = 1 Hz is also observed in thiophenes 6 and 7. (b) The downfield shift for the β-proton in dilithiated 14 relative to the monolithiated 14 is found as well (Figure 2).
-
-
-
-
49
-
-
0346794752
-
-
note
-
The center part of the multiplet is somewhat broadened.
-
-
-
-
50
-
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0035938215
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-
Rajca, A.; Wang, H.; Bolshov, P.; Rajca, S. Tetrahedron 2001, 57, 3725.
-
(2001)
Tetrahedron
, vol.57
, pp. 3725
-
-
Rajca, A.1
Wang, H.2
Bolshov, P.3
Rajca, S.4
-
51
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0034639977
-
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Rajca, A.; Safronov, A.; Rajca, S.; Wongsriratanakul, J. J. Am. Chem. Soc. 2000, 122, 3351.
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J. Am. Chem. Soc.
, vol.122
, pp. 3351
-
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Rajca, A.1
Safronov, A.2
Rajca, S.3
Wongsriratanakul, J.4
-
52
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0001010836
-
-
Yamada, K.; Nakagawa, H.; Kawazura, H. Bull. Chem. Soc. Jpn. 1986, 59, 2429.
-
(1986)
Bull. Chem. Soc. Jpn.
, vol.59
, pp. 2429
-
-
Yamada, K.1
Nakagawa, H.2
Kawazura, H.3
-
53
-
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0347425279
-
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note
-
(a) 3,3′-Bithianaphthenyl 19: mp 82-83°C (lit mp 82.7-83.0 °C).
-
-
-
-
54
-
-
84985195714
-
-
these authors report 72% yield of 'pink solid' of 19, prior to column chromatography and recrystallization
-
(b) Wynberg, H.; Cabell, M. J. Org. Chem. 1973, 38, 2814; these authors report 72% yield of 'pink solid' of 19, prior to column chromatography and recrystallization.
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(1973)
J. Org. Chem.
, vol.38
, pp. 2814
-
-
Wynberg, H.1
Cabell, M.2
|