-
1
-
-
84942320882
-
-
Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam
-
(a) Photochromism - Molecules and Systems; Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 2003.
-
(2003)
Photochromism - Molecules and Systems
-
-
-
2
-
-
0004240038
-
-
Feringa, B. L., Ed.: Wiley-VCH: Weinheim
-
(b) Molecular Switches; Feringa, B. L., Ed.: Wiley-VCH: Weinheim, 2001.
-
(2001)
Molecular Switches
-
-
-
3
-
-
0003464709
-
-
Crano, J. C., Guglielmetti, R. J., Eds.; Kluwer Academic/Plenum Publisher: New York
-
(c) Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Kluwer Academic/Plenum Publisher: New York, 1999.
-
(1999)
Organic Photochromic and Thermochromic Compounds
-
-
-
4
-
-
0004284861
-
-
El'tsov, A. V., Ed.; Consultants Bureau: New York
-
(d) Organic Photochromes; El'tsov, A. V., Ed.; Consultants Bureau: New York, 1990.
-
(1990)
Organic Photochromes
-
-
-
5
-
-
0000527186
-
Special Issue: Photochromism: Memories and Switches
-
Irie, M., Ed.
-
(e) Special Issue: Photochromism: Memories and Switches, Irie, M., Ed. Chem. Rev. 2000, 100, 1683-1890.
-
(2000)
Chem. Rev.
, vol.100
, pp. 1683-1890
-
-
-
6
-
-
33748241762
-
-
(f) Willner, I.; Rubin, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 367-385.
-
(1996)
Angew. Chem., Int. Ed. Engl.
, vol.35
, pp. 367-385
-
-
Willner, I.1
Rubin, S.2
-
7
-
-
23744464557
-
-
Hecht, S. Small 2005, 1, 26-29.
-
(2005)
Small
, vol.1
, pp. 26-29
-
-
Hecht, S.1
-
10
-
-
84942322948
-
-
Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam
-
For reviews, consult: (b) Rau, H. In Photochromism - Molecules and Systems: Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 2003; pp 165-192.
-
(2003)
Photochromism - Molecules and Systems
, pp. 165-192
-
-
Rau, H.1
-
11
-
-
33749150880
-
-
El'tsov, A. V., Ed.; Consultants Bureau: New York
-
(c) Fanghänel, D.; Timpe, G.; Orthman, V. In Organic Photochromes; El'tsov, A. V., Ed.; Consultants Bureau: New York, 1990; pp 105-177.
-
(1990)
Organic Photochromes
, pp. 105-177
-
-
Fanghänel, D.1
Timpe, G.2
Orthman, V.3
-
13
-
-
33749143178
-
-
Peters, M. V.; Goddard, R.; Hecht, S. J. Org. Chem. 2006, 71, 7846-7849.
-
(2006)
J. Org. Chem.
, vol.71
, pp. 7846-7849
-
-
Peters, M.V.1
Goddard, R.2
Hecht, S.3
-
14
-
-
0001938751
-
-
Kadish, K., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego.
-
For a review, consult: Lindsey, J. S. In The Porphyrin Handbook; Kadish, K., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego. 1999; Vol. 1, pp 45-118.
-
(1999)
The Porphyrin Handbook
, vol.1
, pp. 45-118
-
-
Lindsey, J.S.1
-
15
-
-
0141634145
-
-
(a) Lim, Y.-K.; Lee, K.-S.; Cho, C.-G. Org. Lett. 2003, 5, 979-982.
-
(2003)
Org. Lett.
, vol.5
, pp. 979-982
-
-
Lim, Y.-K.1
Lee, K.-S.2
Cho, C.-G.3
-
16
-
-
1842526003
-
-
(b) Lim, Y.-K.; Choi, S.; Park, K. B.; Cho, C.-G. J. Org. Chem. 2004, 69, 2603-2606.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 2603-2606
-
-
Lim, Y.-K.1
Choi, S.2
Park, K.B.3
Cho, C.-G.4
-
17
-
-
0008373415
-
-
It should be noted that the formation of azobenzenes from condensation of nitrosobenzenes with anilines in acetic acid, frequently referred to as the Mills reaction: (a) Mills, C. J. Chem. Soc. 1895, 67, 925-933,
-
(1895)
J. Chem. Soc.
, vol.67
, pp. 925-933
-
-
Mills, C.1
-
18
-
-
84970889989
-
-
was first described by Baeyer: (b) Baeyer, A. Chem. Ber. 1874, 7, 1638-1640.
-
(1874)
Chem. Ber.
, vol.7
, pp. 1638-1640
-
-
Baeyer, A.1
-
19
-
-
33749118325
-
-
See the Supporting Information
-
See the Supporting Information.
-
-
-
-
20
-
-
0029944797
-
-
Rose, E.; Kossanyi, A.; Quelquejeu, M.; Soleilhavoup, M.; Duwavran, F.; Bernard, N.; Lecas, A. J. Am. Chem. Soc. 1996, 118, 1567-1568.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 1567-1568
-
-
Rose, E.1
Kossanyi, A.2
Quelquejeu, M.3
Soleilhavoup, M.4
Duwavran, F.5
Bernard, N.6
Lecas, A.7
-
21
-
-
84982058570
-
-
The synthesis of differently connected oligo(azobenzene)s has been been pioneered by Ruggli and co-workers, who exploited iterative Mills coupling and nitro-reduction sequences. For o-bis(phenylazo)benzenes, see: (a) Ruggli, P.; Rohner, J. HelIv. Chim. Acta 1942, 25, 1533-1542.
-
(1942)
HelIv. Chim. Acta
, vol.25
, pp. 1533-1542
-
-
Ruggli, P.1
Rohner, J.2
-
25
-
-
31944433330
-
-
Similar synthetic problems have recently been encountered in the construction of oligomers containing m-bis(phenylazo)benzenes: Tie, C.; Gallucci, J. C.; Parquette, J. R. J. Am. Chem. Soc. 2006, 128, 1162-1171.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 1162-1171
-
-
Tie, C.1
Gallucci, J.C.2
Parquette, J.R.3
-
28
-
-
0000927698
-
-
A potential route via nitration of 2-amino-4-tert-butyltoluene failed in our hands and gave complex product mixtures, contradictory to literature reports: Rosevear, J.; Wilshire, J. F. K. Aust. J. Chem. 1985, 38, 723-733.
-
(1985)
Aust. J. Chem.
, vol.38
, pp. 723-733
-
-
Rosevear, J.1
Wilshire, J.F.K.2
-
29
-
-
84942714846
-
-
L
-
Smith, D.; L.; Barrett, E. K. Actda Crystallogr., Sect B: Struct. Crystallogr. Cryst. Chem. 1969, 25, 2355-2361.
-
(1969)
Actda Crystallogr., Sect B: Struct. Crystallogr. Cryst. Chem.
, vol.25
, pp. 2355-2361
-
-
Smith, D.1
Barrett, E.K.2
-
30
-
-
13244277640
-
-
Kurth, M. J.; Olmstead, M. M.; Haddadin, M. J. J. Org. Chem. 2005, 70, 1060-1062.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 1060-1062
-
-
Kurth, M.J.1
Olmstead, M.M.2
Haddadin, M.J.3
-
32
-
-
0035980303
-
-
The intramolecular coordination of the o-phenylazo group to various heteroatoms has been exploited. For silicon, see: (a) Kano, N.; Komatsu, F.; Kawashima, T. J. Am. Chem. Soc. 2001, 123, 10778-10779.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 10778-10779
-
-
Kano, N.1
Komatsu, F.2
Kawashima, T.3
-
33
-
-
0142074882
-
-
(b) Kano, N.; Yamamura, M.; Komatsu, F.; Kawashima, T. J. Organomet. Chem. 2003, 686, 192-197.
-
(2003)
J. Organomet. Chem.
, vol.686
, pp. 192-197
-
-
Kano, N.1
Yamamura, M.2
Komatsu, F.3
Kawashima, T.4
-
34
-
-
2442691541
-
-
(c) Kano, N.; Yamamura, M.; Kawashima, T. J. Am. Chem. Soc. 2004, 126, 6250-6251.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 6250-6251
-
-
Kano, N.1
Yamamura, M.2
Kawashima, T.3
-
35
-
-
33744792048
-
-
(d) Kano, N.; Komatsu, F.; Yamamura, M.; Kawashima, T. J. Am. Chem. Soc. 2006, 128, 7097-7109.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 7097-7109
-
-
Kano, N.1
Komatsu, F.2
Yamamura, M.3
Kawashima, T.4
-
36
-
-
24944558511
-
-
For boron, see: (e) Kano, N.; Yoshino, J.; Kawashima, T. Org. Lett. 2005, 7, 3909-3911.
-
(2005)
Org. Lett.
, vol.7
, pp. 3909-3911
-
-
Kano, N.1
Yoshino, J.2
Kawashima, T.3
-
37
-
-
24144440442
-
-
For phosphorous, see: (f) Yamamura, M.; Kano, N.; Kawashima, T. J. Am. Chem. Soc. 2005, 127, 11954-11955.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 11954-11955
-
-
Yamamura, M.1
Kano, N.2
Kawashima, T.3
-
38
-
-
33749152872
-
-
A thorough literature survey reveals that some initial evidence for this type of rearrangement involving azobenzene precursors carrying either o-aldehyde or o-acetal groups dates back to work by Freundler: (a) Freundler, M. P. Bull. Soc. Chim. Fr. 1904, 31, 862-867.
-
(1904)
Bull. Soc. Chim. Fr.
, vol.31
, pp. 862-867
-
-
Freundler, M.P.1
-
40
-
-
21544433782
-
-
The formation of 2H-indazolone derivatives from azobenzene precursors has been reported in a few cases with the following ortho substituents. For hydroxymethyl groups, see: (a) Freundler, M. P. Bull. Soc. Chim. Fr. 1903, 29, 742-747.
-
(1903)
Bull. Soc. Chim. Fr.
, vol.29
, pp. 742-747
-
-
Freundler, M.P.1
-
41
-
-
0000567955
-
-
For ketones, see: (b) Alberti, A.; Bedogni, N.; Benaglia, M.; Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Org. Chem. 1992, 57, 607-613.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 607-613
-
-
Alberti, A.1
Bedogni, N.2
Benaglia, M.3
Leardini, R.4
Nanni, D.5
Pedulli, G.F.6
Tundo, A.7
Zanardi, G.8
-
43
-
-
2342662623
-
-
A search of the Beilstein database reveals more than 23000 entries of different azobenzene derivatives. In the few cases reporting o-(arylazo)arylaldehydes, an alternative structural assignment to the respective 2H-indazolone derivatives seems plausible: (a) Karamé, I.; Jahjah, M.; Messaoudi, A.; Tommasino, M. L.; Lemaire, M. Tetrahedron: Asymmetry 2004, 15, 1569-1581.
-
(2004)
Tetrahedron: Asymmetry
, vol.15
, pp. 1569-1581
-
-
Karamé, I.1
Jahjah, M.2
Messaoudi, A.3
Tommasino, M.L.4
Lemaire, M.5
-
44
-
-
0036402839
-
-
(b) Radbakrishnan, T.; Kolawole, G. A.; Revaprasadu, N.; Nair, P. S.; Sreekala, N. B. Synth. React. Inorg. Met.-Org. Chem. 2002, 32, 1153-1175.
-
(2002)
Synth. React. Inorg. Met.-Org. Chem.
, vol.32
, pp. 1153-1175
-
-
Radbakrishnan, T.1
Kolawole, G.A.2
Revaprasadu, N.3
Nair, P.S.4
Sreekala, N.B.5
-
45
-
-
33749118126
-
-
(c) Saleh, A. A.; Aly, F. M.; El-Baradie, K.; El-Dken, A. A. Egypt. J. Chem. 1990, 33, 255-266.
-
(1990)
Egypt. J. Chem.
, vol.33
, pp. 255-266
-
-
Saleh, A.A.1
Aly, F.M.2
El-Baradie, K.3
El-Dken, A.A.4
-
47
-
-
33749120617
-
-
The oldest literature precedent of controversial assignment of an o-(arylazo)arylaldehyde is related to the so-called "Azoopiansä ure", the product of reducing 2-formyl-5,6-dimethoxy-3-nitrobenzoic acid with zinc under acidic conditions: (a) Prinz, O. J. Prakt. Chem. 1881, 24, 353-374.
-
(1881)
J. Prakt. Chem.
, vol.24
, pp. 353-374
-
-
Prinz, O.1
-
49
-
-
85028907654
-
-
(c) Grüne, H. Chem. Ber. 1886, 19, 2299-2305.
-
(1886)
Chem. Ber.
, vol.19
, pp. 2299-2305
-
-
Grüne, H.1
-
51
-
-
0001574564
-
-
Franz, J. A.; Barrows, R. D.; Camaioni, D. M. J. Am. Chem. Soc. 1984, 106, 3964-3967.
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 3964-3967
-
-
Franz, J.A.1
Barrows, R.D.2
Camaioni, D.M.3
-
52
-
-
0035891639
-
-
Wolters, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803-3805.
-
(2001)
Org. Lett.
, vol.3
, pp. 3803-3805
-
-
Wolters, M.1
Klapars, A.2
Buchwald, S.L.3
|