Selective formation of either Tröger's base or spiro Tröger's base derivatives from [2-aminoporphyrinato(2-)]nickel by choice of reaction conditions

Tetrahedron Letters

Volumn 53, Issue 45, 2012, Pages 6015-6017

  Tatar, Ameneh ^a   Dolenský, Bohumil ^a   Dvořáková, Hana ^a   Král, Vladimír ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Bis(metalloporphyrin); Selectivity; Solvent effect; Spiro Tr ger's base derivative; Tr ger's base derivative

Indexed keywords

[2 AMINOPORPHYRINATO(2)]NICKEL; AMINOMETALLOPORPHYRIN; BASE; BIS(METALLOPORPHYRIN) DERIVATIVE; FORMALDEHYDE; METALLOPORPHYRIN; NICKEL COMPLEX; PYRROLE DERIVATIVE; TROGER BASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; DERIVATIZATION; NITRATION; REACTION TIME; REDUCTION;

EID: 84867246334     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.097     Document Type: Article

References (29)

1. The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Gillard, R., Eds.; Academic: San Diego, USA, 2000.
2. I. Beletskaya, V.S. Tyurin, A.Yu. Tsivadze, R. Guilard, and C. Stern Chem. Rev. 109 2009 1659
3. Recent examples Z.-H. Loh, S.E. Miller, C.J. Chang, S.D. Carpenter, and D.G. Nocera J. Phys. Chem. A 106 2002 11700
4. R. Rein, M. Gross, and N. Solladié Chem. Commun. 1992 2004
5. G.M. Mamardashvili, I.A. Shinkar', N.Zh. Mamardashvili, and O.I. Koifman Russ. J. Coord. Chem. 33 2007 774
6. N. Berova, G. Pescitelli, A.G. Petrovic, and G. Proni Chem. Commun. 2009 5958
7. The recent reviews on Tröger's bases B. Dolenský, J. Elguero, V. Král, C. Pardo, and M. Valík Adv. Heterocycl. Chem. 93 2007 1
8. S. Sergeyev Helv. Chim. Acta 92 2009 415
9. M.J. Crossley, T.W. Hambley, L.G. Mackay, A.C. Try, and R. Walton J. Chem. Soc., Chem. Commun. 1995 1077
10. P.R. Brotherhood, R.A.-S. Wu, P. Turner, and M.J. Crossley Chem. Commun. 2007 225
11. M.J. Crossley, L.G. Mackay, and A.C. Try J. Chem. Soc., Chem. Commun. 1995 1925
12. P.R. Allen, J.N.H. Reek, A.C. Try, and M.J. Crossley Tetrahedron: Asymm. 8 1997 1161
13. J.A. Hutchison, P.J. Sintic, M.J. Crossley, T. Nagamura, and K.P. Ghiggino Phys. Chem. Chem. Phys. 11 2009 3478
14. P.R. Brotherhood, I.J. Luck, I.M. Blake, P. Jensen, P. Turner, and M.J. Crossley Chem. Eur. J. 14 2008 10967
15. M.J. Crossley, A.C. Try, and R. Walton Tetrahedron Lett. 37 1996 6807
16. P.J.E.W. Sintic, Z. Ou, J. Shao, J.A. McDonald, Z.-L. Cai, K.M. Kadish, M.J. Crossley, and J.R. Reimers Phys. Chem. Chem. Phys. 10 2008 515
17. J.E. Baldwin, M.J. Crossley, and J. DeBernardis Tetrahedron 38 1982 685
18. M.M. Catalano, M.J. Crossley, M.M. Harding, and L.G. King J. Chem. Soc., Chem. Commun. 1984 1535
19. S. Ostrowski, D. Szerszeń, and M. Ryszczuk Synthesis 2005 819
20. Bis-Tröger's bases were independently introduced by C. Pardo, E. Sesmilo, E. Gutiérrez-Puebla, A. Monge, J. Elguero, and A. Fruchier J. Org. Chem. 66 2001 1607
21. M. Valík, B. Dolenský, H. Petříč ková, and V. Král Coll. Czech Chem. Commun. 67 2002 609
22. B. Dolenský, M. Havlík, and V. Král Chem. Soc. Rev. 41 2012 3839
23. A. Tatar, J. Čejka, V. Král, and B. Dolenský Org. Lett. 12 2010 1872
24. M. Valík, B. Dolenský, H. Petříč ková, P. Vašek, and V. Král Tetrahedron Lett. 44 2003 2083
25. P.R. Brotherhood, I.J. Luck, and M.J. Crossley Magn. Reson. Chem. 47 2009 257
26. A. Antipas, and M. Gouterman J. Am. Chem. Soc. 105 1983 4896
27. D. Didier, B. Tylleman, N. Lambert, C.M.L. Vande Velde, F. Blockhuys, A. Collas, and S. Sergeyev Tetrahedron 64 2008 6252
28. S. Sergeyev, S. Stas, A. Remacle, C.M.L. Vande Velde, B. Dolenský, M. Havlík, V. Král, and J. Čejka Tetrahedron: Asymm. 20 2009 1918
29. B. Dolenský, V. Parchaňský, P. Matějka, M. Havlík, P. Bouř, and V. Král J. Mol. Struct. 996 2011 69