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Volumn 44, Issue 15, 2005, Pages 5523-5529

Anthracene-induced turnover enhancement in the manganese porphyrin-catalyzed epoxidation of olefins

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ANTHRACENE; ANTHRACENE DERIVATIVE; EPOXIDE; MANGANESE(III) PORPHYRIN; METALLOPORPHYRIN; ORGANOMETALLIC COMPOUND;

EID: 23244446998     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0505596     Document Type: Article
Times cited : (25)

References (33)
  • 4
    • 33544463773 scopus 로고    scopus 로고
    • note
    • IIITPP, however, is shown by experiments with with 5,10-dipyridyl and 5,10,15,20-tetrapyridyl analogues of the tetraphenylporphyrin catalyst.
  • 5
    • 33544472924 scopus 로고    scopus 로고
    • note
    • Included as Supporting Information are extended TON versus time plots for all additives examined. Consistent with Figure 1, those showing TON amplification after 5 min showed additional amplification at longer times.
  • 8
    • 33544469346 scopus 로고    scopus 로고
    • note
    • We thank Prof. Craig Hill for suggesting this interesting possibility.
  • 10
    • 0011697055 scopus 로고
    • See, for example: Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
    • (1992) Chem. Rev. , vol.92 , pp. 1411-1456
    • Meunier, B.1
  • 14
    • 33544464943 scopus 로고    scopus 로고
    • note
    • Presumably the oxo-bridged iron dimer is thermodynamically more stable with respect to dissociation into monometallic components, via oxygen atom transfer, than is the manganese porphyrin dimer. While the doubly bridged salen compound may be similarly stabilized, such stability is probably less relevant, since loss of salen catalytic activity appears to be due mainly to irreversible ligand oxidation.
  • 15
    • 33544456220 scopus 로고    scopus 로고
    • note
    • More rapid cycling through B will also diminish the rate of anthracene consumption via cycle A. An additional factor, however, may be an ability of the most reactive substrates to react also with the dimer (albeit slowly), thus supplanting to some extent the role of anthracene as catalyst regenerator.
  • 21
    • 33544470917 scopus 로고    scopus 로고
    • note
    • Consistent with this suggestion, pyridine addition to a deactivated porphyrin catalyst is observed to restore activity for styrene epoxidation, although less efficaciously than anthracene addition. Accompanying the restored catalytic activity is pyridine N-oxide formation. Addition of the N-oxide to a deactivated catalyst, on the other hand, has no restorative effect.
  • 22
    • 0034596888 scopus 로고    scopus 로고
    • Collman and co-workers (Inorg. Chem., 2000, 39, 4625-4629) have presented evidence for another interesting role for pyridine. They find that conversion of pyridine to pyridine N-oxide renders the ligand a better donor to manganese, thereby enhancing its catalytic activity.
    • (2000) Inorg. Chem. , vol.39 , pp. 4625-4629
    • Collman1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.