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Volumn 50, Issue 2, 2011, Pages 472-476

Facile dearomatization of nitrobenzene derivatives and other nitroarenes with N-benzyl azomethine ylide

Author keywords

azomethine ylides; cycloaddition; dearomatization; nitroarene; polycycles

Indexed keywords

AROMATICITIES; AZOMETHINE YLIDES; DEAROMATIZATION; DERIVATIZATIONS; HIGH YIELD; NITROARENES; NITROBENZENE DERIVATIVE; POLYCYCLES; POLYCYCLIC ADDUCTS; ROOM TEMPERATURE; TRIFLUOROACETIC ACIDS;

EID: 78650903117     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201005779     Document Type: Article
Times cited : (76)

References (59)
  • 1
    • 78650895282 scopus 로고    scopus 로고
    • Hydrogenation reactions
    • Hydrogenation reactions
  • 3
    • 0037448329 scopus 로고    scopus 로고
    • Birch reductions and Birch reductive alkylations
    • J. A. Widegren, R. G. Finke, J. Mol. Catal. A 2003, 191, 187-207. Birch reductions and Birch reductive alkylations
    • (2003) J. Mol. Catal. A , vol.191 , pp. 187-207
    • Widegren, J.A.1    Finke, R.G.2
  • 10
    • 77349122065 scopus 로고    scopus 로고
    • Reactions involving the formation of transition metal complexes
    • L. Pouységu, D. Deffieux, S. Quideau, Tetrahedron 2010, 66, 2235-2261. Reactions involving the formation of transition metal complexes
    • (2010) Tetrahedron , vol.66 , pp. 2235-2261
    • Pouységu, L.1    Deffieux, D.2    Quideau, S.3
  • 22
    • 49849100686 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 5060-5062
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5060-5062
  • 24
    • 78650918834 scopus 로고    scopus 로고
    • For example see
    • For example see
  • 26
    • 0000629986 scopus 로고
    • in (Eds.: B.-M. Trost, I. Fleming), Pergamon, Oxford
    • A. Padwa, in Comprehensive Organic Synthesis Vol.-4 (Eds.:, B.-M. Trost, I. Fleming,), Pergamon, Oxford, 1991, pp.- 1069-1168.
    • (1991) Comprehensive Organic Synthesis Vol.-4 , pp. 1069-1168
    • Padwa, A.1
  • 27
    • 68949219787 scopus 로고
    • Benzene, chlorobenzene, and dichlorobenzene have been reported to behave as a dienophile when heated with hexachloropentadiene at 220-240 °C and under a pressure of 10 kbar for 20-h. No yield is reported. See
    • Benzene, chlorobenzene, and dichlorobenzene have been reported to behave as a dienophile when heated with hexachloropentadiene at 220-240 °C and under a pressure of 10 kbar for 20-h. No yield is reported. See:, W. Jarre, D. Bienek, F. Korte, Angew. Chem. 1975, 87, 201-202
    • (1975) Angew. Chem. , vol.87 , pp. 201-202
    • Jarre, W.1    Bienek, D.2    Korte, F.3
  • 29
    • 78650924498 scopus 로고    scopus 로고
    • Metal-complexed benzene derivatives have been described as diene or dienophile in [4+2] cycloadditions. See
    • Metal-complexed benzene derivatives have been described as diene or dienophile in [4+2] cycloadditions. See
  • 33
    • 78650919549 scopus 로고    scopus 로고
    • See ref.-[1k-l]
    • See ref.-[1k-l].
  • 39
    • 26844568111 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 6272-6276
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 6272-6276
  • 44
    • 78650855242 scopus 로고    scopus 로고
    • The azomethine ylide 2 undergoes several competitive dimerization and oligomerization reactions which effectively decrease the amount of usable 2. The excess 3 reported in this paper parallels in some ways the stability of the substrate.
    • The azomethine ylide 2 undergoes several competitive dimerization and oligomerization reactions which effectively decrease the amount of usable 2. The excess 3 reported in this paper parallels in some ways the stability of the substrate.
  • 45
    • 78650853430 scopus 로고    scopus 로고
    • The number of equivalents used in this reaction is what is required for the reaction to reach completion. Only the tricyclic adduct was isolated and no trace of a bicyclic adduct was ever observed during or after the transformation, presumably because of the much higher reactivity of the intermediate nitrodiene. Notably, no tetracycle was ever formed in this reaction.
    • The number of equivalents used in this reaction is what is required for the reaction to reach completion. Only the tricyclic adduct was isolated and no trace of a bicyclic adduct was ever observed during or after the transformation, presumably because of the much higher reactivity of the intermediate nitrodiene. Notably, no tetracycle was ever formed in this reaction.
  • 46
    • 78650859730 scopus 로고    scopus 로고
    • See the Supporting Information.
    • See the Supporting Information.
  • 47
    • 78650923792 scopus 로고    scopus 로고
    • No trace of the alternate putative cycloadduct A was formed, probably a result of steric reasons.
    • No trace of the alternate putative cycloadduct A was formed, probably a result of steric reasons.
  • 49
    • 78650862033 scopus 로고    scopus 로고
    • 1H-NMR spectrum of the crude reaction mixture.
    • 1H-NMR spectrum of the crude reaction mixture.
  • 50
    • 78650890170 scopus 로고    scopus 로고
    • Both the inductive and mesomeric effects were strong enough to generate complete chemoselectivity in favor of the unsubstituted carbon-carbon double bond.
    • Both the inductive and mesomeric effects were strong enough to generate complete chemoselectivity in favor of the unsubstituted carbon-carbon double bond.
  • 51
    • 33846366253 scopus 로고    scopus 로고
    • Gribble has recently reported the reaction of nitroindoles with an analogous azomethine ylide.
    • Gribble has recently reported the reaction of nitroindoles with an analogous azomethine ylide:, S. Roy, T. L. S. Kishbaugh, J. P. Jasinski, G. W. Gribble, Tetrahedron Lett. 2007, 48, 1313-1316.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 1313-1316
    • Roy, S.1    Kishbaugh, T.L.S.2    Jasinski, J.P.3    Gribble, G.W.4
  • 54
    • 78650917694 scopus 로고    scopus 로고
    • CCDC-793306 (31) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC-793306 (31) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
  • 57
    • 0001858137 scopus 로고
    • 1 type involving the loss of nitrite ion and its readdition after cyclization can also be considered.
    • 1 type involving the loss of nitrite ion and its readdition after cyclization can also be considered.
    • (1990) Aldrichimica Acta , vol.23 , pp. 71-78
    • Kornblum, N.1
  • 58
    • 78650907652 scopus 로고    scopus 로고
    • [21] with 4 to deliver the new radical-cation B which, upon subsequent interaction with 2, would generate product 32 en route to the cycloadduct 5, and another equivalent of 34.
    • [21] with 4 to deliver the new radical-cation B which, upon subsequent interaction with 2, would generate product 32 en route to the cycloadduct 5, and another equivalent of 34.
  • 59
    • 78650870107 scopus 로고    scopus 로고
    • Radical-cation 34 could also be produced from ylide 2 and traces of oxygen. However, the fact that the reactions were carried out under inert atmosphere renders this possibility unlikely.
    • Radical-cation 34 could also be produced from ylide 2 and traces of oxygen. However, the fact that the reactions were carried out under inert atmosphere renders this possibility unlikely.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.