메뉴 건너뛰기




Volumn 11, Issue 11, 2005, Pages 3427-3442

Synthesis of mono- And disubstituted porphyrins: A- and 5,10-A 2-type systems

Author keywords

Heterocycles; Macrocycles; Nitrogen; Nucleophilic addition; Porphyrinoids; Tetrapyrroles

Indexed keywords

ADDITION REACTIONS; ANISOTROPY; COLUMN CHROMATOGRAPHY; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DERIVATIVES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RECRYSTALLIZATION (METALLURGY); SILICA GEL; SINGLE CRYSTALS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 19844369992     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500001     Document Type: Article
Times cited : (91)

References (126)
  • 3
    • 0001938751 scopus 로고    scopus 로고
    • (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York
    • a) J. S. Lindsey in The Porphyrin Handbook Vol. 1 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, pp. 45-118;
    • (2000) The Porphyrin Handbook , vol.1 , pp. 45-118
    • Lindsey, J.S.1
  • 4
    • 0000700975 scopus 로고    scopus 로고
    • (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York
    • b) M. G. H. Vicente in The Porphyrin Handbook, Vol. 1 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, pp. 149-199;
    • (2000) The Porphyrin Handbook , vol.1 , pp. 149-199
    • Vicente, M.G.H.1
  • 5
    • 0000052647 scopus 로고    scopus 로고
    • (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York
    • L. Jaquinod in The Porphyrin Handbook, Vol.1 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, pp. 201-237.
    • (2000) The Porphyrin Handbook , vol.1 , pp. 201-237
    • Jaquinod, L.1
  • 7
    • 19844379457 scopus 로고    scopus 로고
    • note
    • [2a] and uses capital letters to denote the arrangement and type of individual meso substituents.
  • 8
    • 0002226421 scopus 로고    scopus 로고
    • (Eds: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York
    • K. Smith in The Porphyrin Handbook, Vol. 1 (Eds: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, pp. 1-43.
    • (2000) The Porphyrin Handbook , vol.1 , pp. 1-43
    • Smith, K.1
  • 14
    • 0032482052 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 1107-1109;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1107-1109
  • 56
    • 0001688871 scopus 로고    scopus 로고
    • (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego
    • a) M. O. Senge in The Porphyrin Handbook, Vol. 1 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, pp. 239-347;
    • (2000) The Porphyrin Handbook , vol.1 , pp. 239-347
    • Senge, M.O.1
  • 58
    • 0034602318 scopus 로고    scopus 로고
    • Additional information for this rationale is derived from earlier results of mixed condensation reactions using both pivalaldehyde and tolylaldehyde. Although all possible statistical isomers were obtained at the porphyrinogen, porphomethene, or porphodimethene stage, the 5,10-di-tert-butylated product could never be isolated as the fully oxidized porphyrin. See: M. O. Senge, S. Runge, M. Speck, K. Ruhlandt-Senge, Tetrahedron 2000, 56, 8927-8932.
    • (2000) Tetrahedron , vol.56 , pp. 8927-8932
    • Senge, M.O.1    Runge, S.2    Speck, M.3    Ruhlandt-Senge, K.4
  • 63
    • 19844379235 scopus 로고    scopus 로고
    • note
    • b) Besides the good yields (70-80%), an additional advantage of this method is the formation of porphine in high purity in solution. This greatly facilitates purification and subsequent use in other reactions. A constant disadvantage of older methods was not so much the formation of porphine in sufficient quantity but the separation of the target compound from the polymeric mixture of other products formed during condensation reactions. Impure porphine is almost impossible to dissolve. Isopropanol can be used instead of 1-butanol.
  • 64
    • 19844379456 scopus 로고    scopus 로고
    • Dissertation, Freie Universität Berlin (Germany)
    • a) S. Hatscher, Dissertation, Freie Universität Berlin (Germany), 2003;
    • (2003)
    • Hatscher, S.1
  • 73
    • 19844370525 scopus 로고    scopus 로고
    • E. Nickel, IPN: WO 00/52012, 2000, CAN 133:207748
    • e) E. Nickel, IPN: WO 00/52012, 2000, CAN 133:207748;
  • 74
    • 19844364381 scopus 로고    scopus 로고
    • note
    • [28a]
  • 75
    • 19844365322 scopus 로고    scopus 로고
    • note
    • [8b-d]
  • 76
    • 19844372674 scopus 로고    scopus 로고
    • note
    • [31]
  • 91
    • 19844380263 scopus 로고    scopus 로고
    • note
    • [28a]
  • 115
    • 2442623104 scopus 로고    scopus 로고
    • Compound 14a was also recently observed as a product of the detert-butylation of 5,10,15,20-tetra(t-butyl)porphyrin: P. Kuś, M. Stefaniak, Monatsh. Chem. 2004, 135, 509-511.
    • (2004) Monatsh. Chem. , vol.135 , pp. 509-511
    • Kuś, P.1    Stefaniak, M.2
  • 116
    • 19844372424 scopus 로고    scopus 로고
    • note
    • [16] However, in several cases only fragmentary experimental details are available;
  • 125
    • 0004150157 scopus 로고    scopus 로고
    • Program for the Solution of Crystal Structures, Universität Göttingen, Göttingen (Germany)
    • a) G. M. Sheldrick, SHELXS-93, Program for the Solution of Crystal Structures, Universität Göttingen, Göttingen (Germany), 1993;
    • (1993) SHELXS-93
    • Sheldrick, G.M.1
  • 126
    • 0004150157 scopus 로고    scopus 로고
    • Program for the Refinement of Crystal Structures, Universität Göttingen, Göttingen (Germany)
    • b) G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, Universität Göttingen, Göttingen (Germany), 1997.
    • (1997) SHELXL-97
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.