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Volumn 63, Issue 15, 1998, Pages 5164-5168

Rate Increase in Consecutive Nucleophilic Aromatic Substitution Reactions of Trichlorotrinitrobenzene: The Synthesis of 1-(Alkylamino)-3,5-dichloro-2,4,6-trinitrobenzenes

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Indexed keywords


EID: 0000490910     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980374z     Document Type: Article
Times cited : (14)

References (44)
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    • Gerard, F.; Hardy A.; Becuwe, A. Acta Crystallogr., Sect. C 1993, 49, 1215-1218. Computations at the HF 6-31G* level also find that nitrobenzene with the nitro group in the planar conformation is more susceptible to attack by nucleophiles than with the nitro group in the perpendicular conformation: Politzer, P.; Lane, P.; Jayasuriya, K.; Domelsmith, L. N. J. Am. Chem. Soc. 1987, 109, 1899-1901.
    • (1993) Acta Crystallogr., Sect. C , vol.49 , pp. 1215-1218
    • Gerard, F.1    Hardy, A.2    Becuwe, A.3
  • 23
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    • Gerard, F.; Hardy A.; Becuwe, A. Acta Crystallogr., Sect. C 1993, 49, 1215-1218. Computations at the HF 6-31G* level also find that nitrobenzene with the nitro group in the planar conformation is more susceptible to attack by nucleophiles than with the nitro group in the perpendicular conformation: Politzer, P.; Lane, P.; Jayasuriya, K.; Domelsmith, L. N. J. Am. Chem. Soc. 1987, 109, 1899-1901.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 1899-1901
    • Politzer, P.1    Lane, P.2    Jayasuriya, K.3    Domelsmith, L.N.4
  • 24
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    • NH⋯ON hydrogen bonds have been described as weaker as comparable OH⋯ON interactions. However, they are structure-determining even in intermolecular cases; see, for example: Panunto, T. W.; Urbànczyk-Lipkowska, Z.; Johnson, R.; Etter, M. C. J. Am. Chem. Soc. 1987, 109, 7786-7797. For semiempirical computations of their strength, see, for example: Vinson, L. K.; Dannenberg, J. J. J. Am. Chem. Soc. 1989, 111, 2777-2781.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 7786-7797
    • Panunto, T.W.1    Urbànczyk-Lipkowska, Z.2    Johnson, R.3    Etter, M.C.4
  • 25
    • 33845184074 scopus 로고
    • NH⋯ON hydrogen bonds have been described as weaker as comparable OH⋯ON interactions. However, they are structure-determining even in intermolecular cases; see, for example: Panunto, T. W.; Urbànczyk-Lipkowska, Z.; Johnson, R.; Etter, M. C. J. Am. Chem. Soc. 1987, 109, 7786-7797. For semiempirical computations of their strength, see, for example: Vinson, L. K.; Dannenberg, J. J. J. Am. Chem. Soc. 1989, 111, 2777-2781.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2777-2781
    • Vinson, L.K.1    Dannenberg, J.J.2
  • 26
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    • A planarizing effect of intramolecular hydrogen bonds has been noted in the comparison of the crystal structures of picramide and its N-methyl-, and N-ethyl-, and N,N-dimethyl derivatives: Butcher, R. J.; Gilardi, R.; Flippen-Anderson, J. L.; George, C. New J. Chem. 1992, 16, 679-692.
    • (1992) New J. Chem. , vol.16 , pp. 679-692
    • Butcher, R.J.1    Gilardi, R.2    Flippen-Anderson, J.L.3    George, C.4
  • 28
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    • See the Supporting Information. The authors have also deposited atomic coordinates for 2a with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK
    • See the Supporting Information. The authors have also deposited atomic coordinates for 2a with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
  • 37
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    • Engelbertz, P. (Inv.), Chemische Fabrik Griesheim, D.R.P. 767510, 1936; Chem. Abstr. 1955, 49, 14803d.
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    • Hill, M. E.; Taylor, F., Jr. J. Org. Chem. 1960, 25, 1037-1038. Note: 266.5 g of oleum is required, not 266.5 mL, as written. The formation of 1,2,3,5-tetrachloro-4,6-dinitrobenzene is minimal under these conditions (ca. 2%; unpublished observations). For the kinetics of this nitration process, see: Moodie, R. B.; Payne, M. A.; Schofield, K. J. Chem. Soc., Perkin Trans. 2 1985, 1457-1464.
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    • Hill, M.E.1    Taylor Jr., F.2
  • 39
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    • Hill, M. E.; Taylor, F., Jr. J. Org. Chem. 1960, 25, 1037-1038. Note: 266.5 g of oleum is required, not 266.5 mL, as written. The formation of 1,2,3,5-tetrachloro-4,6-dinitrobenzene is minimal under these conditions (ca. 2%; unpublished observations). For the kinetics of this nitration process, see: Moodie, R. B.; Payne, M. A.; Schofield, K. J. Chem. Soc., Perkin Trans. 2 1985, 1457-1464.
    • (1985) J. Chem. Soc., Perkin Trans. 2 , pp. 1457-1464
    • Moodie, R.B.1    Payne, M.A.2    Schofield, K.3


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