-
1
-
-
0000605623
-
-
Kadish, K. M, Smith, K. M, Guilard, R, Eds, Academic Press: San Diego
-
(a) Sessler, J. L.; Gebauer, A.; Vogel, E. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 2, pp 1-54.
-
(2000)
The Porphyrin Handbook
, vol.2
, pp. 1-54
-
-
Sessler, J.L.1
Gebauer, A.2
Vogel, E.3
-
2
-
-
0002484311
-
-
Kadish, K. M, Smith, K. M, Guilard, R, Eds, Academic Press: San Diego
-
(b) Sessler, J. L.; Gebauer, A.; Weghorn, S. J. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 2, pp 55-124.
-
(2000)
The Porphyrin Handbook
, vol.2
, pp. 55-124
-
-
Sessler, J.L.1
Gebauer, A.2
Weghorn, S.J.3
-
3
-
-
0001004194
-
-
Kadish, K. M, Smith, K. M, Guilard, R, Eds, Academic Press: San Diego
-
(c) Lash, T. D. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 2, pp 125-200.
-
(2000)
The Porphyrin Handbook
, vol.2
, pp. 125-200
-
-
Lash, T.D.1
-
4
-
-
34547135422
-
-
For recent leading examples, see: a
-
For recent leading examples, see: (a) Muthiah, C.; Bhaumik, J.; Lindsey, J. S. J. Org. Chem. 2007, 72, 5839-5842.
-
(2007)
J. Org. Chem
, vol.72
, pp. 5839-5842
-
-
Muthiah, C.1
Bhaumik, J.2
Lindsey, J.S.3
-
5
-
-
33947635677
-
-
(b) Ptaszek, M.; McDowell, B. E.; Taniguchi, M.; Kim, H.-J.; Lindsey, J. S. Tetrahedron 2007, 63, 3826-3839.
-
(2007)
Tetrahedron
, vol.63
, pp. 3826-3839
-
-
Ptaszek, M.1
McDowell, B.E.2
Taniguchi, M.3
Kim, H.-J.4
Lindsey, J.S.5
-
6
-
-
33947700461
-
-
(c) Taniguchi, M.; Ptaszek, M.; McDowell, B. E.; Lindsey, J. S. Tetrahedron 2007, 63, 3840-3849.
-
(2007)
Tetrahedron
, vol.63
, pp. 3840-3849
-
-
Taniguchi, M.1
Ptaszek, M.2
McDowell, B.E.3
Lindsey, J.S.4
-
7
-
-
33947694765
-
-
(d) Taniguchi, M.; Ptaszek, M.; McDowell, B. E.; Boyle, P. D.; Lindsey, J. S. Tetrahedron 2007, 63, 3850-3863.
-
(2007)
Tetrahedron
, vol.63
, pp. 3850-3863
-
-
Taniguchi, M.1
Ptaszek, M.2
McDowell, B.E.3
Boyle, P.D.4
Lindsey, J.S.5
-
9
-
-
47049121842
-
-
(f) Borbas, K. E.; Ruzié, C.; Lindsey, J. S. Org. Lett. 2008, 10, 1931-1934.
-
(2008)
Org. Lett
, vol.10
, pp. 1931-1934
-
-
Borbas, K.E.1
Ruzié, C.2
Lindsey, J.S.3
-
10
-
-
34848916658
-
-
(g) Muthiah, C.; Ptaszek, M.; Nguyen, T. M.; Flack, K. M.; Lindsey, J. S. J. Org. Chem. 2007, 72, 7736-7749.
-
(2007)
J. Org. Chem
, vol.72
, pp. 7736-7749
-
-
Muthiah, C.1
Ptaszek, M.2
Nguyen, T.M.3
Flack, K.M.4
Lindsey, J.S.5
-
11
-
-
48249097149
-
-
and references therein
-
(h) Ruzié, C.; Krayer, M.; Balasubramanian, T.; Lindsey, J. S. J. Org. Chem. 2008, 73, 5806-5820, and references therein.
-
(2008)
J. Org. Chem
, vol.73
, pp. 5806-5820
-
-
Ruzié, C.1
Krayer, M.2
Balasubramanian, T.3
Lindsey, J.S.4
-
12
-
-
33947334208
-
-
Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32, 476.
-
(1967)
J. Org. Chem
, vol.32
, pp. 476
-
-
Adler, A.D.1
Longo, F.R.2
Finarelli, J.D.3
Goldmacher, J.4
Assour, J.5
Korsakoff, L.6
-
13
-
-
0002439873
-
-
Sessler, J. L.; Mozaffari, A.; Johnson, M. R. Org. Synth. 1992, 70, 68-78.
-
(1992)
Org. Synth
, vol.70
, pp. 68-78
-
-
Sessler, J.L.1
Mozaffari, A.2
Johnson, M.R.3
-
14
-
-
0001935323
-
-
For reviews covering chlorin syntheses, see: a
-
For reviews covering chlorin syntheses, see: (a) Flitsch, W. Adv. Heterocycl. Chem. 1988, 43, 73-126.
-
(1988)
Adv. Heterocycl. Chem
, vol.43
, pp. 73-126
-
-
Flitsch, W.1
-
15
-
-
0032560210
-
-
(b) Sternberg, E. D.; Dolphin, D.; Brückner, C. Tetrahedron 1998, 54, 4151-4202.
-
(1998)
Tetrahedron
, vol.54
, pp. 4151-4202
-
-
Sternberg, E.D.1
Dolphin, D.2
Brückner, C.3
-
17
-
-
33748236741
-
-
Chang, C. K.; Wu, W.; Chern, S.-S.; Peng, S.-M. Angew. Chem., Int. Ed. Engl. 1992, 31, 70-72.
-
(1992)
Angew. Chem., Int. Ed. Engl
, vol.31
, pp. 70-72
-
-
Chang, C.K.1
Wu, W.2
Chern, S.-S.3
Peng, S.-M.4
-
18
-
-
33845185113
-
-
Gouterman, M.; Hall, R. J.; Khalil, G.-E.; Martin, P. C.; Shankland, E. G.; Cerny, R. L. J. Am. Chem. Soc. 1989, 111, 3702-3707.
-
(1989)
J. Am. Chem. Soc
, vol.111
, pp. 3702-3707
-
-
Gouterman, M.1
Hall, R.J.2
Khalil, G.-E.3
Martin, P.C.4
Shankland, E.G.5
Cerny, R.L.6
-
23
-
-
37049085087
-
-
(a) Adams, K. R.; Bonnett, R.; Burke, P. J.; Salgado, A.; Vallés, M. A. J. Chem. Soc., Chem. Commun. 1993, 1860-1861.
-
(1993)
J. Chem. Soc., Chem. Commun
, pp. 1860-1861
-
-
Adams, K.R.1
Bonnett, R.2
Burke, P.J.3
Salgado, A.4
Vallés, M.A.5
-
24
-
-
33748586269
-
-
(b) Adams, K. R.; Bonnett, R.; Burke, P. J.; Salgado, A.; Vallés, M. A. J. Chem. Soc., Perkin Trans. 1 1997, 1769-1772.
-
(1997)
J. Chem. Soc., Perkin Trans. 1
, pp. 1769-1772
-
-
Adams, K.R.1
Bonnett, R.2
Burke, P.J.3
Salgado, A.4
Vallés, M.A.5
-
25
-
-
0033556065
-
-
Kozyrev, A. N.; Alderfer, J. L.; Dougherty, T. J.; Pandey, R. K. Angew. Chem., Int. Ed. 1999, 38, 126-128.
-
(1999)
Angew. Chem., Int. Ed
, vol.38
, pp. 126-128
-
-
Kozyrev, A.N.1
Alderfer, J.L.2
Dougherty, T.J.3
Pandey, R.K.4
-
26
-
-
33750521803
-
-
(a) Köpke, T.; Pink, M.; Zaleski, J. M. Org. Biomol. Chem. 2006, 4, 4059-4062.
-
(2006)
Org. Biomol. Chem
, vol.4
, pp. 4059-4062
-
-
Köpke, T.1
Pink, M.2
Zaleski, J.M.3
-
28
-
-
0037968998
-
-
Brückner, C.; Rettig, S. J.; Dolphin, D. J. Org. Chem. 1998, 63, 2094-2098.
-
(1998)
J. Org. Chem
, vol.63
, pp. 2094-2098
-
-
Brückner, C.1
Rettig, S.J.2
Dolphin, D.3
-
29
-
-
0037981255
-
-
McCarthy, J. R.; Jenkins, H. A.; Brückner, C. Org. Lett. 2003, 5, 19-22.
-
(2003)
Org. Lett
, vol.5
, pp. 19-22
-
-
McCarthy, J.R.1
Jenkins, H.A.2
Brückner, C.3
-
30
-
-
0033599519
-
-
Brückner, C.; Sternberg, E. D.; MacAlpine, J. K.; Rettig, S. J.; Dolphin, D. J. Am. Chem. Soc. 1999, 121, 2609-2610.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 2609-2610
-
-
Brückner, C.1
Sternberg, E.D.2
MacAlpine, J.K.3
Rettig, S.J.4
Dolphin, D.5
-
31
-
-
19944422435
-
-
Brückner, C.; Hyland, M. A.; Sternberg, E. D.; MacAlpine, J.; Rettig, S. J.; Patrick, B. O.; Dolphin, D. Inorg. Chim. Acta 2005, 358, 2943-2953.
-
(2005)
Inorg. Chim. Acta
, vol.358
, pp. 2943-2953
-
-
Brückner, C.1
Hyland, M.A.2
Sternberg, E.D.3
MacAlpine, J.4
Rettig, S.J.5
Patrick, B.O.6
Dolphin, D.7
-
32
-
-
2942674701
-
-
McCarthy, J. R.; Hyland, M. A.; Brückner, C. Org. Biomol. Chem. 2004, 2, 1484-1491.
-
(2004)
Org. Biomol. Chem
, vol.2
, pp. 1484-1491
-
-
McCarthy, J.R.1
Hyland, M.A.2
Brückner, C.3
-
33
-
-
2942654430
-
-
Daniell, H. W.; Brückner, C. Angew. Chem., Int. Ed. 2004, 43, 1688-1691.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 1688-1691
-
-
Daniell, H.W.1
Brückner, C.2
-
34
-
-
13644259122
-
-
Lara, K. K.; Rinaldo, C. K.; Brückner, C. Tetrahedron 2005, 61, 2529-2539.
-
(2005)
Tetrahedron
, vol.61
, pp. 2529-2539
-
-
Lara, K.K.1
Rinaldo, C.K.2
Brückner, C.3
-
35
-
-
66349132766
-
-
Ryppa, C.; Niedzwiedzki, D.; Morozowich, N. L.; Rapole, S.; Zeller, M.; Frank, H. A.; Brückner, C. Chem.- Eur. J. 2009, 15, 5749-5762.
-
(2009)
Chem.- Eur. J
, vol.15
, pp. 5749-5762
-
-
Ryppa, C.1
Niedzwiedzki, D.2
Morozowich, N.L.3
Rapole, S.4
Zeller, M.5
Frank, H.A.6
Brückner, C.7
-
36
-
-
41849143015
-
-
For recent representative examples, see: a
-
For recent representative examples, see: (a) Matano, Y.; Matsumoto, K.; Nakao, Y.; Uno, H.; Sakaki, S.; Imahori, H. J. Am. Chem. Soc. 2008, 130, 4588-4589.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 4588-4589
-
-
Matano, Y.1
Matsumoto, K.2
Nakao, Y.3
Uno, H.4
Sakaki, S.5
Imahori, H.6
-
37
-
-
34447331463
-
-
(b) Hisaki, I.; Hiroto, S.; Kim, K. S.; Noh, S. B.; Kim, D.; Shinokubo, H.; Osuka, A. Angew. Chem., Int. Ed. 2007, 46, 5125-5128.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 5125-5128
-
-
Hisaki, I.1
Hiroto, S.2
Kim, K.S.3
Noh, S.B.4
Kim, D.5
Shinokubo, H.6
Osuka, A.7
-
38
-
-
41549112946
-
-
(c) Kelley, R. F.; Lee, S. J.; Wilson, T. M.; Nakamura, Y.; Tiede, D. M.; Osuka, A.; Hupp, J. T.; Wasielewski, M. R. J. Am. Chem. Soc. 2008, 130, 4277-4284.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 4277-4284
-
-
Kelley, R.F.1
Lee, S.J.2
Wilson, T.M.3
Nakamura, Y.4
Tiede, D.M.5
Osuka, A.6
Hupp, J.T.7
Wasielewski, M.R.8
-
39
-
-
34250840097
-
-
(d) Esdaile, L. J.; Jensen, P.; McMurtrie, J. C.; Arnold, D. P. Angew. Chem., Int. Ed. 2007, 46, 2090-2093.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 2090-2093
-
-
Esdaile, L.J.1
Jensen, P.2
McMurtrie, J.C.3
Arnold, D.P.4
-
40
-
-
33745867249
-
-
(e) Lysenko, A. B.; Thamyongkit, P.; Schmidt, I.; Diers, J. R.; Bocian, D. F.; Lindsey, J. S. J. Porphyrins Phthalocyanines 2006, 10, 22-32.
-
(2006)
J. Porphyrins Phthalocyanines
, vol.10
, pp. 22-32
-
-
Lysenko, A.B.1
Thamyongkit, P.2
Schmidt, I.3
Diers, J.R.4
Bocian, D.F.5
Lindsey, J.S.6
-
41
-
-
56449089593
-
-
and references therein
-
(f) Song, H.; Kirmaier, C.; Taniguchi, M.; Diers, J. R.; Bocian, D. F.; Lindsey, J. S.; Holten, D. J. Am. Chem. Soc. 2008, 130, 15636-15648, and references therein.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 15636-15648
-
-
Song, H.1
Kirmaier, C.2
Taniguchi, M.3
Diers, J.R.4
Bocian, D.F.5
Lindsey, J.S.6
Holten, D.7
-
42
-
-
67650422789
-
-
The decomposition is often accompanied by the forming of a green, polar (Rf) 0.10, silica-CH2Cl2, and unstable compound. We tentatively assigned it, based on its morpholinochlorin-like UV-vis spectrum and mass ESI+ HR-MS, 100% MeCN, m/z found 665.2548, corresponding to C44H33N4O3, expected mass 665.2553, as the hydrate structure 2H2·; H2O. Correspondingly, it can be converted by addition of EtOH, under acid catalysis, in high yield to morpholinochlorin 1H2. However, attempts to isolate and fully characterize this compound failed, Chemical Equation Presented
-
2. However, attempts to isolate and fully characterize this compound failed. (Chemical Equation Presented)
-
-
-
-
44
-
-
67650422791
-
-
Intramolecular Cannizzaro reactions of aromatic vic-bisaldehydes: (b) McDonald, R. S.; Sibley, C. E. Can. J. Chem. 1981, 59, 1061-1067.
-
Intramolecular Cannizzaro reactions of aromatic vic-bisaldehydes: (b) McDonald, R. S.; Sibley, C. E. Can. J. Chem. 1981, 59, 1061-1067.
-
-
-
-
45
-
-
37049078446
-
-
(c) Bowden, K.; El-Kaissi, F. A.; Ranson, R. J. J. Chem. Soc., Perkin Trans. 2 1990, 2089-2092.
-
(1990)
J. Chem. Soc., Perkin Trans. 2
, pp. 2089-2092
-
-
Bowden, K.1
El-Kaissi, F.A.2
Ranson, R.J.3
-
47
-
-
67650466551
-
-
Ph.D. Thesis, University of Connecticut
-
McCarthy, J. R. Ph.D. Thesis, University of Connecticut, 2003.
-
(2003)
-
-
McCarthy, J.R.1
-
48
-
-
0142196132
-
-
McCarthy, J. R.; Melfi, P. J.; Capetta, S. H.; Brückner, C. Tetrahedron 2003, 59, 9137-9146.
-
(2003)
Tetrahedron
, vol.59
, pp. 9137-9146
-
-
McCarthy, J.R.1
Melfi, P.J.2
Capetta, S.H.3
Brückner, C.4
-
49
-
-
17044452031
-
-
Brückner, C.; McCarthy, J. R.; Daniell, H. W.; Pendon, Z. D.; Ilagan, R. P.; Francis, T. M.; Ren, L.; Birge, R. R.; Frank, H. A. Chem. Phys. 2003, 294, 285-303.
-
(2003)
Chem. Phys
, vol.294
, pp. 285-303
-
-
Brückner, C.1
McCarthy, J.R.2
Daniell, H.W.3
Pendon, Z.D.4
Ilagan, R.P.5
Francis, T.M.6
Ren, L.7
Birge, R.R.8
Frank, H.A.9
-
50
-
-
67650483858
-
-
All the assignments were backed by H,H and H,C-COSY measurements; see the Supporting Information
-
All the assignments were backed by H,H and H,C-COSY measurements; see the Supporting Information.
-
-
-
-
51
-
-
0028566853
-
-
(a) Barloy, L.; Dolphin, D.; Dupré, D.; Wijesekera, T. P. J. J. Org. Chem. 1994, 59, 7976-7985.
-
(1994)
J. Org. Chem
, vol.59
, pp. 7976-7985
-
-
Barloy, L.1
Dolphin, D.2
Dupré, D.3
Wijesekera, T.P.J.4
-
52
-
-
33748578357
-
-
Review article
-
(b) Review article: Fox, S.; Boyle, R. W. Tetrahedron 2006, 62, 10039-10054.
-
(2006)
Tetrahedron
, vol.62
, pp. 10039-10054
-
-
Fox, S.1
Boyle, R.W.2
-
53
-
-
0029818482
-
-
For an example of a chlorin dimer, see: a
-
For an example of a chlorin dimer, see: (a) Jaquinod, L.; Nurco, D. J.; Medforth, C. J.; Pandey, R. K.; Forsyth, T. P.; Olmstead, M. M.; Smith, K. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1013-1016.
-
(1996)
Angew. Chem., Int. Ed. Engl
, vol.35
, pp. 1013-1016
-
-
Jaquinod, L.1
Nurco, D.J.2
Medforth, C.J.3
Pandey, R.K.4
Forsyth, T.P.5
Olmstead, M.M.6
Smith, K.M.7
-
54
-
-
58849101382
-
-
For examples of the 1H NMR shifts expressed by directly β,β′-linked porphyrin dimers, see: (b) Bringmann, G, Götz, D. C. G, Gulder, T. A. M, Gehrke, T. H, Bruhn, T, Kupfer, T, Radacki, K, Braunschweig, H, Heckmann, A, Lambert, C. J. Am. Chem. Soc. 2008, 133, 17812-17825
-
1H NMR shifts expressed by directly β,β′-linked porphyrin dimers, see: (b) Bringmann, G.; Götz, D. C. G.; Gulder, T. A. M.; Gehrke, T. H.; Bruhn, T.; Kupfer, T.; Radacki, K.; Braunschweig, H.; Heckmann, A.; Lambert, C. J. Am. Chem. Soc. 2008, 133, 17812-17825.
-
-
-
-
55
-
-
33748849549
-
-
Hunter, C. A.; Sanders, J. K. M.; Stone, A. J. Chem. Phys. 1989, 133, 395-404.
-
(1989)
J. Chem. Phys
, vol.133
, pp. 395-404
-
-
Hunter, C.A.1
Sanders, J.K.M.2
Stone, A.3
-
56
-
-
0000835279
-
-
Kadish, K. M, Smith, K. M, Guilard, R, Eds, Academic Press: San Diego
-
(a) Shelnutt, J. A. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 7, pp 167-224.
-
(2000)
The Porphyrin Handbook
, vol.7
, pp. 167-224
-
-
Shelnutt, J.A.1
-
57
-
-
0031078856
-
-
(b) Jentzen, W.; Song, X.-Z.; Shelnutt, J. A. J. Phys. Chem. B. 1997, 101, 1684-1699.
-
(1997)
J. Phys. Chem. B
, vol.101
, pp. 1684-1699
-
-
Jentzen, W.1
Song, X.-Z.2
Shelnutt, J.A.3
-
58
-
-
67650422790
-
-
Song, L, Shelnutt, J. A. NSD Engine Version 3.0
-
(c) Song, L.; Shelnutt, J. A. NSD Engine Version 3.0 (http://jasheln.unm. edu/jasheln/content/nsd/NSDengine/start.htm).
-
-
-
-
59
-
-
29944437988
-
-
Zeller, M.; Hunter, A. D.; McCarthy, J. R.; Capetta, S. H.; Brückner, C. J. Chem. Crystallogr. 2005, 35, 935-942.
-
(2005)
J. Chem. Crystallogr
, vol.35
, pp. 935-942
-
-
Zeller, M.1
Hunter, A.D.2
McCarthy, J.R.3
Capetta, S.H.4
Brückner, C.5
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