Standard Article

Displacement and ipso-Substitution in Nitration

Amino, Nitroso, Nitro and Related Groups (1996)

  1. J. P. B. Sandall

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0091

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Sandall, J. P. B. 2009. Displacement and ipso-Substitution in Nitration. Patai's Chemistry of Functional Groups. .

Author Information

  1. University of Exeter, Department of Chemistry, Exeter, UK

Publication History

  1. Published Online: 15 DEC 2009

Chemistry Terms

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Abstract

  • 1
    Introduction
  • 2
    Formation of ipso-Adducts
  • 3
    Further Reactions of ipso-Intermediates and Adducts
  • 4
    Rearrangement of ipso-Substituted Groups
  • 5
    Displacement of ipso-Substituted Groups
  • 6
    Conclusion

Keywords:

  • displacement and ipso-substitution in nitration;
  • ipso-adduct formation;
  • ipso-substituted group rearrangement;
  • displacement of ipso-substituted groups;
  • nucleophilic substitution and ipso-substitution as norm;
  • ipso-intermediates and adducts;
  • ipso-species behaviour and Hartshorn’s group;
  • displacement of groups under ipso-attack in indoles

Featured Compounds

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  1. 1 - 46
Compound 1
Molecular Weight:211.2145
Molecular Formula:C10H13NO4
InChIKey:IIDISDSNYLXXLU-UHFFFAOYSA-N
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Compound 2
Molecular Weight:211.2145
Molecular Formula:C10H13NO4
InChIKey:IIDISDSNYLXXLU-MGCOHNPYSA-N
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Compound 3
Molecular Weight:197.1879
Molecular Formula:C9H11NO4
InChIKey:CUKYVKDURSIYKZ-BDAKNGLRSA-N
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Compound 4
Molecular Weight:169.1778
Molecular Formula:C8H11NO3
InChIKey:KANSIYZPDUCPAA-UHFFFAOYSA-N
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Compound 5
Molecular Weight:181.2112
Molecular Formula:C9H13N2O2
InChIKey:WJMMVENCERBQGW-UHFFFAOYSA-N
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Compound 6
Molecular Weight:209.2643
Molecular Formula:C11H17N2O2
InChIKey:VDTMMZMKRMLRCG-UHFFFAOYSA-N
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Compound 7
Molecular Weight:181.1885
Molecular Formula:C9H11NO3
InChIKey:GIJJCRSSEPOOBR-UHFFFAOYSA-N
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Compound 8
Molecular Weight:245.1464
Molecular Formula:C7H7N3O7
InChIKey:LHMLTRDZOZWAHI-UHFFFAOYSA-N
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Compound 9
Molecular Weight:153.1354
Molecular Formula:C7H7NO3
InChIKey:SKGFPCMAFZIZGL-UHFFFAOYSA-N
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Compound 10
Molecular Weight:468.879
Molecular Formula:C8H9Br3N2O6
InChIKey:RDMKDRJRDQITOI-MUEPXWKYSA-N
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Compound 11
Molecular Weight:468.879
Molecular Formula:C8H9Br3N2O6
InChIKey:RDMKDRJRDQITOI-JZJLSFIKSA-N
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Compound 12
Molecular Weight:265.348
Molecular Formula:C15H23NO3
InChIKey:XVPLVFIJPIVZIZ-UHFFFAOYSA-N
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Compound 13
Molecular Weight:370.4406
Molecular Formula:C18H30N2O6
InChIKey:IQUPUGVYFBRMHQ-UHFFFAOYSA-N
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Compound 18
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:NKTOLZVEWDHZMU-UHFFFAOYSA-N
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Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:KUFFULVDNCHOFZ-UHFFFAOYSA-N
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Compound 16
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:CKJAETQXQRJXLM-UHFFFAOYSA-N
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Compound 15
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:JVWYGOHRDHHENE-UHFFFAOYSA-N
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Compound 19
Molecular Weight:236.224
Molecular Formula:C11H12N2O4
InChIKey:ZCDPUAQHMGGROW-UHFFFAOYSA-N
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Compound 20
Molecular Weight:231.633
Molecular Formula:C9H10ClNO4
InChIKey:XBQPVMUQSUMRKD-UHFFFAOYSA-N
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Compound 23
Molecular Weight:330.036
Molecular Formula:C7H5Cl2N3O8
InChIKey:ONSNMMRXTKXLSC-NJGYIYPDSA-N
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Compound 24
Molecular Weight:254.024
Molecular Formula:C7H5Cl2NO5
InChIKey:YGVMATFHTLOGQF-FSPLSTOPSA-N
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Compound 25
Molecular Weight:292.2475
Molecular Formula:C12H12N4O5
InChIKey:BJCHYRHMHMRFTM-UHFFFAOYSA-N
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Compound 26
Molecular Weight:263.2493
Molecular Formula:C12H13N3O4
InChIKey:GTWINNSVLSGODC-UHFFFAOYSA-N
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Compound 27
Molecular Weight:245.234
Molecular Formula:C12H11N3O3
InChIKey:JSFHYLRKSMUONS-UHFFFAOYSA-N
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Compound 28
Molecular Weight:201.2212
Molecular Formula:C12H11NO2
InChIKey:MTGHZAUDWJOXGX-UHFFFAOYSA-N
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Compound 29
Molecular Weight:292.2475
Molecular Formula:C12H12N4O5
InChIKey:LPFUTIOWHJUEBC-NEPJUHHUSA-N
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Compound 30
Molecular Weight:292.2475
Molecular Formula:C12H12N4O5
InChIKey:LPFUTIOWHJUEBC-RYUDHWBXSA-N
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Compound 37
Molecular Weight:307.645
Molecular Formula:C9H10ClN3O7
InChIKey:PTCSVWUNHKBOLQ-CIUDSAMLSA-N
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Compound 38
Molecular Weight:307.645
Molecular Formula:C9H10ClN3O7
InChIKey:PTCSVWUNHKBOLQ-VGMNWLOBSA-N
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Compound 31
Molecular Weight:200.2365
Molecular Formula:C12H12N2O
InChIKey:FEDCLOHUEIKYIB-UHFFFAOYSA-N
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Compound 32
Molecular Weight:267.238
Molecular Formula:C11H13N3O5
InChIKey:MGMSVWSPVCKBNA-MWLCHTKSSA-N
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Compound 33
Molecular Weight:267.238
Molecular Formula:C11H13N3O5
InChIKey:MGMSVWSPVCKBNA-KOLCDFICSA-N
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Compound 34
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:SHTQXCRYNDMSMM-UHFFFAOYSA-N
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Compound 35
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 36
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 39
Molecular Weight:307.645
Molecular Formula:C9H10ClN3O7
InChIKey:PTCSVWUNHKBOLQ-XHNCKOQMSA-N
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Compound 40
Molecular Weight:307.645
Molecular Formula:C9H10ClN3O7
InChIKey:PTCSVWUNHKBOLQ-HRDYMLBCSA-N
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Compound 41
Molecular Weight:225.2411
Molecular Formula:C11H15NO4
InChIKey:ZXILJGOYDZCATK-UHFFFAOYSA-N
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Compound 42
Molecular Weight:225.2411
Molecular Formula:C11H15NO4
InChIKey:VJMAXVMALASPGP-UHFFFAOYSA-N
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Compound 44
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 46
Molecular Weight:439.721
Molecular Formula:C7H4Br4O2
InChIKey:LUJKEUBHHFQVJL-UHFFFAOYSA-N
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Compound 47
Molecular Weight:222.026
Molecular Formula:C7H5Cl2NO3
InChIKey:CXSFGSGZNMFCPC-UHFFFAOYSA-N
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Compound 48
Molecular Weight:193.027
Molecular Formula:C7H6Cl2O2
InChIKey:MNEVJEMUTRBTIL-UHFFFAOYSA-N
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Compound 49
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 50
Molecular Weight:222.026
Molecular Formula:C7H5Cl2NO3
InChIKey:MGWQBHFMJSAOQF-UHFFFAOYSA-N
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  1. 1 - 46