-
1
-
-
77951813397
-
-
Reviews for zethrene: a) R. Umeda, D. Hibi, K. Miki, Y. Tobe, Pure Appl. Chem. 2010, 82, 871
-
(2010)
Pure Appl. Chem.
, vol.82
, pp. 871
-
-
Umeda, R.1
Hibi, D.2
Miki, K.3
Tobe, Y.4
-
9
-
-
0037111823
-
-
d) T. Morikawa, S. Narita, T.-i. Shibuya, THEOCHEM 2002, 618, 47.
-
(2002)
THEOCHEM
, vol.618
, pp. 47
-
-
Morikawa, T.1
Narita, S.2
Shibuya, T.-I.3
-
10
-
-
10044223336
-
-
a) T. Morikawa, S. Narita, D. J. Klein, J. Chem. Inf. Comput. Sci. 2004, 44, 1891
-
(2004)
J. Chem. Inf. Comput. Sci.
, vol.44
, pp. 1891
-
-
Morikawa, T.1
Narita, S.2
Klein, D.J.3
-
11
-
-
0000608843
-
-
b) M. Randić, Tetrahedron 1975, 31, 1477. Review
-
(1975)
Tetrahedron
, vol.31
, pp. 1477
-
-
Randić, M.1
-
19
-
-
77956902194
-
-
Theoretic studies indicate that the HOMO-LUMO energy gap of zethrene (1a) is almost identical to that of pentacene; see
-
a) T. P. Smith, M. J. Pellerite, T. W. Kelley, D. V. Muyres, D. E. Vogel, K. M. Vogel, L. D. Boardman, T. D. Dunbar, U. S. Pat. Appl. Publ. 2003, pp. 13. Theoretic studies indicate that the HOMO-LUMO energy gap of zethrene (1a) is almost identical to that of pentacene; see
-
(2003)
U. S. Pat. Appl. Publ.
, pp. 13
-
-
Smith, T.P.1
Pellerite, M.J.2
Kelley, T.W.3
Muyres, D.V.4
Vogel, D.E.5
Vogel, K.M.6
Boardman, L.D.7
Dunbar, T.D.8
-
22
-
-
65549153503
-
-
b) M. Nakano, R. Kishi, A. Takebe, M. Nate, H. Takahashi, T. Kubo, K. Kamada, K. Ohta, B. Champagne, E. Botek, Comput. Lett. 2007, 3, 333.
-
(2007)
Comput. Lett.
, vol.3
, pp. 333
-
-
Nakano, M.1
Kishi, R.2
Takebe, A.3
Nate, M.4
Takahashi, H.5
Kubo, T.6
Kamada, K.7
Ohta, K.8
Champagne, B.9
Botek, E.10
-
23
-
-
0000035632
-
-
D. Désilets, P. M. Kazmaier, R. A. Burt, Can. J. Chem. 1995, 73, 319.
-
(1995)
Can. J. Chem.
, vol.73
, pp. 319
-
-
Désilets, D.1
Kazmaier, P.M.2
Burt, R.A.3
-
24
-
-
70349129646
-
-
E. Clar, K. Lang, H. Schulz-Kiesow, Chem. Ber. 1955, 88, 1520.
-
(1955)
Chem. Ber.
, vol.88
, pp. 1520
-
-
Clar, E.1
Lang, K.2
Schulz-Kiesow, H.3
-
27
-
-
0001112511
-
-
a) H. A. Staab, A. Nissen, J. Ipaktschi, Angew. Chem. 1968, 80, 241;
-
(1968)
Angew. Chem.
, vol.80
, pp. 241
-
-
Staab, H.A.1
Nissen, A.2
Ipaktschi, J.3
-
30
-
-
0001208281
-
-
X-ray crystal structure of 7, 8, 15, 16-tetradehydrocyclodeca[1, 2, 3-de :6, 7, 8- d'e']dinaphthalene (3)
-
c) H. A. Staab, J. Ipaktschi, A. Nissen, Chem. Ber. 1971, 104, 1182; X-ray crystal structure of 7, 8, 15, 16-tetradehydrocyclodeca[1, 2, 3-de :6, 7, 8- d'e']dinaphthalene (3)
-
(1971)
Chem. Ber.
, vol.104
, pp. 1182
-
-
Staab, H.A.1
Ipaktschi, J.2
Nissen, A.3
-
31
-
-
70349116966
-
-
d) R. Umeda, D. Hibi, K. Miki, Y. Tobe, Org. Lett. 2009, 11, 4104.
-
(2009)
Org. Lett.
, vol.11
, pp. 4104
-
-
Umeda, R.1
Hibi, D.2
Miki, K.3
Tobe, Y.4
-
33
-
-
84987553912
-
-
b) R. Gleiter, H. P. Schaff, H. Rodewald, R. Jahn, H. Irngartinger, Helv. Chim. Acta 1987, 70, 480
-
(1987)
Helv. Chim. Acta
, vol.70
, pp. 480
-
-
Gleiter, R.1
Schaff, H.P.2
Rodewald, H.3
Jahn, R.4
Irngartinger, H.5
-
34
-
-
3242705276
-
-
a) W. Huang, X. Zhou, K.-i. Kanno, T. Takahashi, Org. Lett. 2004, 6, 2429
-
(2004)
Org. Lett.
, vol.6
, pp. 2429
-
-
Huang, W.1
Zhou, X.2
Kanno, K.-I.3
Takahashi, T.4
-
36
-
-
0041888449
-
-
c) S. Kawasaki, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 6836
-
(2003)
J. Org. Chem.
, vol.68
, pp. 6836
-
-
Kawasaki, S.1
Satoh, T.2
Miura, M.3
Nomura, M.4
-
37
-
-
0001375982
-
-
d) R. C. Larock, M. J. Doty, Q. Tian, J. M. Zenner, J. Org. Chem. 1997, 62, 7536
-
(1997)
J. Org. Chem.
, vol.62
, pp. 7536
-
-
Larock, R.C.1
Doty, M.J.2
Tian, Q.3
Zenner, J.M.4
-
40
-
-
62349115878
-
-
Reviews
-
g) T. Kawase, A. Konishi, Y. Hirao, K. Matsumoto, H. Kurata, T. Kubo, Chem. Eur. J. 2009, 15, 2653. Reviews
-
(2009)
Chem. Eur. J.
, vol.15
, pp. 2653
-
-
Kawase, T.1
Konishi, A.2
Hirao, Y.3
Matsumoto, K.4
Kurata, H.5
Kubo, T.6
-
41
-
-
84890980591
-
-
Eds.: P. J. Stang, R. R. Tykwinski, F. Diederich, Wiley-VCH, Weinheim
-
h) R. C. Larock in Acetylene Chemistry: Chemistry, Biology, and Material Science (Eds.: P. J. Stang, R. R. Tykwinski, F. Diederich), Wiley-VCH, Weinheim, 2005, pp.51
-
(2005)
Acetylene Chemistry Chemistry Biology and Material Science
, pp. 51
-
-
Larock In, R.C.1
-
43
-
-
0003441482
-
-
2nd ed. , Wiely, New York
-
j) J. Tsuji, Palladium Reagents and Catalysts, 2nd ed. , Wiely, New York, 2004, p. 231.
-
(2004)
Palladium Reagents and Catalysts
, pp. 231
-
-
Tsuji, J.1
-
44
-
-
77956936668
-
-
See the Supporting Information.
-
See the Supporting Information.
-
-
-
-
46
-
-
77956893296
-
-
The structure of 6 was verified by X-ray crystal analysis (T.-C. Wu, Y.-T. Wu, unpublished results). X-ray crystallographic data for 1a (CCDC762793), 1b (CCDC762790), 1l (CCDC762792), 1r (CCDC762794), 7 (CCDC762791), and 9a(CCDC771823) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
-
The structure of 6 was verified by X-ray crystal analysis (T.-C. Wu, Y.-T. Wu, unpublished results). X-ray crystallographic data for 1a (CCDC762793), 1b (CCDC762790), 1l (CCDC762792), 1r (CCDC762794), 7 (CCDC762791), and 9a(CCDC771823) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
-
-
-
-
47
-
-
77956901113
-
-
In the presence of Pd catalysts and silver salts, hexaphenylben- zene undergoes the partial cyclodehydrogenation to generate 1, 2, 3, 4-tetraphenyltriphenylene; see
-
In the presence of Pd catalysts and silver salts, hexaphenylben- zene undergoes the partial cyclodehydrogenation to generate 1, 2, 3, 4-tetraphenyltriphenylene; see
-
-
-
-
48
-
-
53849118099
-
-
A cycloadduct generated via 1bthrough the full cyclodehydrogenation was not observed. Reviews for Lewis acid-mediated cyclodehydrogenation of polycyclic aromatic hydrocarbons
-
a) Y.-T. Wu, K.-H. Huang, C.-C. Shin, T.-C. Wu, Chem. Eur. J. 2008, 14, 6697. A cycloadduct generated via 1bthrough the full cyclodehydrogenation was not observed. Reviews for Lewis acid-mediated cyclodehydrogenation of polycyclic aromatic hydrocarbons
-
(2008)
Chem. Eur. J.
, vol.14
, pp. 6697
-
-
Wu, Y.-T.1
Huang, K.-H.2
Shin, C.-C.3
Wu, T.-C.4
-
49
-
-
0035353543
-
-
b) M. D. Watson, A. Fechtenkötter, K. Müllen, Chem. Rev. 2001, 101, 1267
-
(2001)
Chem. Rev.
, vol.101
, pp. 1267
-
-
Watson, M.D.1
Fechtenkötter, A.2
Müllen, K.3
-
50
-
-
33947712905
-
-
c) J. Wu, W. Pisula, K. Müllen, Chem. Rev. 2007, 107, 718.
-
(2007)
Chem. Rev.
, vol.107
, pp. 718
-
-
Wu, J.1
Pisula, W.2
Müllen, K.3
-
51
-
-
77952366409
-
-
Y.-H. Kung, Y.-S. Cheng, C.-C. Tai, W.-S. Liu, C.-C. Shin, C.-C. Ma, Y.-C. Tsai, T.-C. Wu, M.-Y. Kuo, Y.-T. Wu, Chem. Eur. J. 2010, 16, 5909.
-
(2010)
Chem. Eur. J.
, vol.16
, pp. 5909
-
-
Kung, Y.-H.1
Cheng, Y.-S.2
Tai, C.-C.3
Liu, W.-S.4
Shin, C.-C.5
Ma, C.-C.6
Tsai, Y.-C.7
Wu, T.-C.8
Kuo, M.-Y.9
Wu, Y.-T.10
-
52
-
-
77956943910
-
-
2) was isolated in 92% yield. Unfortunately, the accurate structure cannot be determined on the basis of 1H and 13C NMR and MS spectra. Crystallization of this compound was not successful because it slowly decomposed
-
2) was isolated in 92% yield. Unfortunately, the accurate structure cannot be determined on the basis of 1H and 13C NMR and MS spectra. Crystallization of this compound was not successful because it slowly decomposed.
-
-
-
-
53
-
-
77956902762
-
-
Phenanthrene with small displacements from exact planarity
-
Phenanthrene with small displacements from exact planarity
-
-
-
-
54
-
-
0002854106
-
-
Some 4, 5-disubstituted phenanthrenes deviate significantly from planarity
-
a) M. I. Kay, Y. Okaya, D. E. Cox, Acta Crystallogr. Sect. B1971, 27, 26. Some 4, 5-disubstituted phenanthrenes deviate significantly from planarity
-
(1971)
Acta Crystallogr. Sect. B
, vol.27
, pp. 26
-
-
Kay, M.I.1
Okaya, Y.2
Cox, D.E.3
-
55
-
-
0001497609
-
-
b) R. Cosmo, T. W. Hambley, S. Sternhell, . Org. Chem. 1987, 52, 3119
-
(1987)
. Org. Chem.
, vol.52
, pp. 3119
-
-
Cosmo, R.1
Hambley, T.W.2
Sternhell, S.3
-
56
-
-
0006560482
-
-
c) F. Imashiro, A. Saika, Z. Taira, J. Org. Chem. 1987, 52, 5727
-
(1987)
J. Org. Chem.
, vol.52
, pp. 5727
-
-
Imashiro, F.1
Saika, A.2
Taira, Z.3
-
57
-
-
0000166575
-
-
6, 8, 15, 17-Tetraphenyl-1.18, 4.5, 9.10, 13.14-tetrabenzoheptacene, which contains phenanthrene substructures, is a twisted acene
-
d) R. N. Armstrong, H. L. Ammon, J. N. Darnow, J. Am. Chem. Soc. 1987, 109, 2077. 6, 8, 15, 17-Tetraphenyl-1.18, 4.5, 9.10, 13.14-tetrabenzoheptacene, which contains phenanthrene substructures, is a twisted acene
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 2077
-
-
Armstrong, R.N.1
Ammon, H.L.2
Darnow, J.N.3
-
58
-
-
0344065646
-
-
A recent review for twisted acenes
-
e) H. M. Duong, M. Bendikov, D. Steiger, Q. Zhang, G. Sonmez, J. Yamada, F. Wudl, Org. Lett. 2003, 5, 4433. A recent review for twisted acenes
-
(2003)
Org. Lett.
, vol.5
, pp. 4433
-
-
Duong, H.M.1
Bendikov, M.2
Steiger, D.3
Zhang, Q.4
Sonmez, G.5
Yamada, J.6
Wudl, F.7
-
60
-
-
77956914707
-
-
Bond alternation (or localization) in aromatic systems is also a method to distinguish between benzene and cyclohexatriene. For example, the bond alternation in tris(bicyclo- [2.1.1]hexeno)benzene is estimated to be 0.089 Å
-
Bond alternation (or localization) in aromatic systems is also a method to distinguish between benzene and cyclohexatriene. For example, the bond alternation in tris(bicyclo- [2.1.1]hexeno)benzene is estimated to be 0.089 Å
-
-
-
-
61
-
-
0001634689
-
-
a) N. L. rank, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1995, 117, 2102
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 2102
-
-
Rank, N.L.1
Baldridge, K.K.2
Siegel, J.S.3
-
62
-
-
0001453409
-
-
b) H.-B. BüK. K. Baldridge, K. Hardcastle, N. L. Frank, P. Gantzel, J. S. Siegel, J. Ziller, Angew. Chem. 1995, 107, 1575
-
(1995)
Angew. Chem.
, vol.107
, pp. 1575
-
-
Bü, H.-B.1
Baldridge, K.K.2
Hardcastle, K.3
Frank, N.L.4
Gantzel, P.5
Siegel, J.S.6
Ziller, J.7
-
63
-
-
33748224437
-
-
Epoxidation and cyclopropanation of tris(bicyclo[2.1.1]hexeno)benzene give triexpoxide and tercyclopropane, respectively, see
-
Angew. Chem. Int. Ed. Engl. 1995, 34, 1454. Epoxidation and cyclopropanation of tris(bicyclo[2.1.1]hexeno)benzene give triexpoxide and tercyclopropane, respectively, see
-
(1995)
Angew. Chem. Int. Ed. Engl.
, vol.34
, pp. 1454
-
-
-
65
-
-
0024733168
-
-
F. L. Arbeloa, P. R. Ojeda, I. L. Arbeloa, J. Lumin. 1989, 44, 105.
-
(1989)
J. Lumin.
, vol.44
, pp. 105
-
-
Arbeloa, F.L.1
Ojeda, P.R.2
Arbeloa, I.L.3
|