Standard Article

Rearrangements of Hydrazo, Azoxy and Azo Compounds: Kinetic, Product and Isotope Studies

Hydrazo, Azo and Azoxy Groups (1997)

  1. Robin A. COX1,
  2. Erwin Buncel2

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0158

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

COX, R. A. and Buncel, E. 2009. Rearrangements of Hydrazo, Azoxy and Azo Compounds: Kinetic, Product and Isotope Studies. Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    University of Toronto, Department of Chemistry, Toronto, Ontario, Canada

  2. 2

    Queen's University, Department of Chemistry, Kingston, Ontario, Canada

Publication History

  1. Published Online: 15 DEC 2009

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

  • 1
    Introduction
  • 2
    Rearrangements of Hydrazo Compounds
  • 3
    Rearrangements of Azoxy Compounds
  • 4
    Rearrangements of Azo Compounds
  • 5
    Acknowledgements

Keywords:

  • rearrangements of hydrazo compounds;
  • acid catalysed benzidine rearrangement;
  • heavy-atom isotope effects;
  • thermal and photochemical benzidine arrangements;
  • rearrangements of axoxy compounds;
  • rearrangements of azo compounds

Featured Compounds

VIEW

  1. 1 - 92
Compound 1
Molecular Weight:184.2371
Molecular Formula:C12H12N2
InChIKey:YBQZXXMEJHZYMB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 2
Molecular Weight:184.2371
Molecular Formula:C12H12N2
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 3
Molecular Weight:184.2371
Molecular Formula:C12H12N2
InChIKey:RDMFEHLCCOQUMH-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 4
Molecular Weight:184.2371
Molecular Formula:C12H12N2
InChIKey:HOLGXWDGCVTMTB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 5
Molecular Weight:184.2371
Molecular Formula:C12H12N2
InChIKey:ATGUVEKSASEFFO-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 6
Molecular Weight:184.2371
Molecular Formula:C12H12N2
InChIKey:NFCPRRWCTNLGSN-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 20
Molecular Weight:127.572
Molecular Formula:C6H6ClN
InChIKey:QSNSCYSYFYORTR-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 38
Molecular Weight:198.2206
Molecular Formula:C12H10N2O
InChIKey:GAUZCKBSTZFWCT-YPKPFQOOSA-N
View compound in article | Full details | Search for this compound
Compound 40
Molecular Weight:198.2206
Molecular Formula:C12H10N2O
InChIKey:BEYOBVMPDRKTNR-BUHFOSPRSA-N
View compound in article | Full details | Search for this compound
Compound 7
Molecular Weight:244.289
Molecular Formula:C14H16N2O2
InChIKey:OVZJNFMCLJEZQV-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 8
Molecular Weight:244.289
Molecular Formula:C14H16N2O2
InChIKey:JRBJSXQPQWSCCF-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 9
Molecular Weight:214.2631
Molecular Formula:C13H14N2O
InChIKey:GYEHMALGJMHWFB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 10
Molecular Weight:214.2631
Molecular Formula:C13H14N2O
InChIKey:RBLUJIWKMSZIMK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 11
Molecular Weight:214.2631
Molecular Formula:C13H14N2O
InChIKey:OSQHCWNKZXXLLZ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 12
Molecular Weight:284.3544
Molecular Formula:C20H16N2
InChIKey:QNLBBCJLGWFZPM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 13
Molecular Weight:234.2958
Molecular Formula:C16H14N2
InChIKey:AMKQRLOPSSMNEC-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 14
Molecular Weight:284.3544
Molecular Formula:C20H16N2
InChIKey:DDAPSNKEOHDLKB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 15
Molecular Weight:267.3239
Molecular Formula:C20H13N
InChIKey:STJXCDGCXVZHDU-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 16
Molecular Weight:253.127
Molecular Formula:C12H10Cl2N2
InChIKey:BVPHWSDABGXRQD-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 19
Molecular Weight:251.111
Molecular Formula:C12H8Cl2N2
InChIKey:XHQLXCFUPJSGOE-FOCLMDBBSA-N
View compound in article | Full details | Search for this compound
Compound 17
Molecular Weight:253.127
Molecular Formula:C12H10Cl2N2
InChIKey:GQLZJDIJIIFRPK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 18
Molecular Weight:218.682
Molecular Formula:C12H11ClN2
InChIKey:NLGIEISQJFZTIS-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 21
Molecular Weight:436.0301
Molecular Formula:C12H10I2N2
InChIKey:SPNRRAJCRLKEQA-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 22
Molecular Weight:328.1608
Molecular Formula:C12H4F8N2
InChIKey:CGFODVIRAZACDC-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 23
Molecular Weight:328.1608
Molecular Formula:C12H4F8N2
InChIKey:FWOLORXQTIGHFX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 24
Molecular Weight:212.2902
Molecular Formula:C14H16N2
InChIKey:OVXBYJMCICSXFP-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 25
Molecular Weight:240.3434
Molecular Formula:C16H20N2
InChIKey:PFVUKZSHRNODFA-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 26
Molecular Weight:240.3434
Molecular Formula:C16H20N2
InChIKey:LUCJTGHFNRWQMY-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 28
Molecular Weight:205.279
Molecular Formula:C10H11N3S
InChIKey:WFWIIESJNLJSQP-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 29
Molecular Weight:205.279
Molecular Formula:C10H11N3S
InChIKey:BEAUMUVRUVYYNY-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 30
Molecular Weight:228.2466
Molecular Formula:C13H12N2O2
InChIKey:ZENCJANXGMPKKK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 31
Molecular Weight:228.2466
Molecular Formula:C13H12N2O2
InChIKey:FBUYPSSREMSFOG-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 32
Molecular Weight:228.2466
Molecular Formula:C13H12N2O2
InChIKey:LRIKELLACRHPOA-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 33
Molecular Weight:184.2167
Molecular Formula:C11H9N3
InChIKey:STGZUKHALNSQAG-BUHFOSPRSA-O
View compound in article | Full details | Search for this compound
Compound 37
Molecular Weight:199.2087
Molecular Formula:C11H9N3O
InChIKey:BCBHUOGPSRNKLW-BUHFOSPRSA-N
View compound in article | Full details | Search for this compound
Compound 35
Molecular Weight:109.1259
Molecular Formula:C6H7NO
InChIKey:PLIKAWJENQZMHA-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 36
Molecular Weight:94.1145
Molecular Formula:C5H6N2
InChIKey:NUKYPUAOHBNCPY-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 41
Molecular Weight:248.2793
Molecular Formula:C16H12N2O
InChIKey:XXNDLVXSJIBQMW-ZCXUNETKSA-N
View compound in article | Full details | Search for this compound
Compound 45
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 46
Molecular Weight:248.2793
Molecular Formula:C16H12N2O
InChIKey:CQYDCXNJLAOBIF-ISLYRVAYSA-N
View compound in article | Full details | Search for this compound
Compound 47
Molecular Weight:199.2087
Molecular Formula:C11H9N3O
InChIKey:VRTYCDQHVOJKMR-YPKPFQOOSA-N
View compound in article | Full details | Search for this compound
Compound 48
Molecular Weight:199.2087
Molecular Formula:C11H9N3O
InChIKey:JDILYYMMHWXCFV-YPKPFQOOSA-N
View compound in article | Full details | Search for this compound
Compound 49
Molecular Weight:201.2234
Molecular Formula:C11H11N3O
InChIKey:DJMIUTJFTPGRLR-UHFFFAOYSA-O
View compound in article | Full details | Search for this compound
Compound 50
Molecular Weight:184.2156
Molecular Formula:C11H10N3
InChIKey:VAIPFNQPMKFVRX-UHFFFAOYSA-O
View compound in article | Full details | Search for this compound
Compound 51
Molecular Weight:199.2087
Molecular Formula:C11H9N3O
InChIKey:BCBHUOGPSRNKLW-BUHFOSPRSA-N
View compound in article | Full details | Search for this compound
Compound 52
Molecular Weight:212.2472
Molecular Formula:C13H12N2O
InChIKey:QBBVVBKEFHNUBO-PFONDFGASA-N
View compound in article | Full details | Search for this compound
Compound 53
Molecular Weight:212.2472
Molecular Formula:C13H12N2O
InChIKey:LOUNBGKTTREKBQ-PFONDFGASA-N
View compound in article | Full details | Search for this compound
Compound 54
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 55
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 57
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 58
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 60
Molecular Weight:282.3801
Molecular Formula:C18H22N2O
InChIKey:XLEROTDLIROTDN-FMQUCBEESA-N
View compound in article | Full details | Search for this compound
Compound 59
Molecular Weight:266.3796
Molecular Formula:C18H22N2
InChIKey:AVWTUUICFCEKDD-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 61
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 62
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 63
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 64
Molecular Weight:342.1443
Molecular Formula:C12H2F8N2O
InChIKey:MBNJVVWZJOOBSY-DQRAZIAOSA-N
View compound in article | Full details | Search for this compound
Compound 65
Molecular Weight:440.653
Molecular Formula:C12HClF8N2O3S
InChIKey:RTAGEXIHTJCIAI-GHVJWSGMSA-N
View compound in article | Full details | Search for this compound
Compound 66
Molecular Weight:326.1438
Molecular Formula:C12H2F8N2
InChIKey:PEZJAQUDUYJMOD-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 67
Molecular Weight:362.1247
Molecular Formula:C12F10N2
InChIKey:SOQPHLBWYFFKJO-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 77
Molecular Weight:198.2206
Molecular Formula:C12H10N2O
InChIKey:PEXGTUZWTLMFID-BUHFOSPRSA-N
View compound in article | Full details | Search for this compound
Compound 68
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 69
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 72
Molecular Weight:244.2256
Molecular Formula:C12H10N3O3
InChIKey:YDUAMBUHSUUBFQ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 73
Molecular Weight:244.2256
Molecular Formula:C12H10N3O3
InChIKey:AHDDHPFJQVEGJD-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 76
Molecular Weight:198.2206
Molecular Formula:C12H10N2O
InChIKey:PLQQAYRCUVTRMR-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 78
Molecular Weight:200.2131
Molecular Formula:C12H10N2O
InChIKey:GAUZCKBSTZFWCT-YPKPFQOOSA-N
View compound in article | Full details | Search for this compound
Compound 79
Molecular Weight:302.323
Molecular Formula:C20H14N2O
InChIKey:MLBRNSRLRXSZGY-DQRAZIAOSA-N
View compound in article | Full details | Search for this compound
Compound 80
Molecular Weight:238.2845
Molecular Formula:C15H14N2O
InChIKey:VMRJQSRWFYBHBO-MSUUIHNZSA-N
View compound in article | Full details | Search for this compound
Compound 83
Molecular Weight:278.3483
Molecular Formula:C18H18N2O
InChIKey:DVRDFGCBMDKRGR-VXPUYCOJSA-N
View compound in article | Full details | Search for this compound
Compound 81
Molecular Weight:238.2845
Molecular Formula:C15H14N2O
InChIKey:YGQOBTFZGIUNAQ-WUKNDPDISA-N
View compound in article | Full details | Search for this compound
Compound 82
Molecular Weight:238.2845
Molecular Formula:C15H14N2O
InChIKey:RXRVIKKWJVKPQB-WUKNDPDISA-N
View compound in article | Full details | Search for this compound
Compound 84
Molecular Weight:296.3636
Molecular Formula:C18H20N2O2
InChIKey:VTEVLDVHHYFUBL-FMQUCBEESA-N
View compound in article | Full details | Search for this compound
Compound 85
Molecular Weight:278.3483
Molecular Formula:C18H18N2O
InChIKey:BCIACIYYROVOAW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 86
Molecular Weight:278.3086
Molecular Formula:C16H14N4O
InChIKey:XGMTZZGLFGXDPS-SDXDJHTJSA-N
View compound in article | Full details | Search for this compound
Compound 87
Molecular Weight:254.3269
Molecular Formula:C16H18N2O
InChIKey:IFYDLKKPIFEVOU-ISLYRVAYSA-N
View compound in article | Full details | Search for this compound
Compound 88
Molecular Weight:248.2793
Molecular Formula:C16H12N2O
InChIKey:MRQIXHXHHPWVIL-ISLYRVAYSA-N
View compound in article | Full details | Search for this compound
Compound 89
Molecular Weight:248.2793
Molecular Formula:C16H12N2O
InChIKey:MRQIXHXHHPWVIL-ISLYRVAYSA-N
View compound in article | Full details | Search for this compound
Compound 90
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 91
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 92
Molecular Weight:452.369
Molecular Formula:C16H12N2Na2O7S2
InChIKey:TXVRKNUZLYFDTJ-KZYDBBBVSA-L
View compound in article | Full details | Search for this compound
Compound 93
Molecular Weight:474.351
Molecular Formula:C16H11N2Na3O7S2
InChIKey:GYEVPBXZSLTJMS-GLCFPVLVSA-K
View compound in article | Full details | Search for this compound
Compound 94
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 95
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 96
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 98
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 99
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 100
Molecular Weight:199.2087
Molecular Formula:C11H9N3O
InChIKey:BCBHUOGPSRNKLW-BUHFOSPRSA-N
View compound in article | Full details | Search for this compound
Compound 101
Molecular Weight:213.2352
Molecular Formula:C12H11N3O
InChIKey:QAHXMHRIMFMINN-CCEZHUSRSA-N
View compound in article | Full details | Search for this compound
Compound 102
Molecular Weight:214.2426
Molecular Formula:C12H12N3O
InChIKey:OOQSNRCLXODVGG-UHFFFAOYSA-O
View compound in article | Full details | Search for this compound
Compound 103
Molecular Weight:215.2511
Molecular Formula:C12H13N3O
InChIKey:FWIQYVDKDNLEIE-BUHFOSPRSA-N
View compound in article | Full details | Search for this compound
Compound 104
Molecular Weight:213.2352
Molecular Formula:C12H11N3O
InChIKey:OOQSNRCLXODVGG-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound

VIEW

  1. 1 - 92