Standard Article

Eliminations Involving Carbon–Halogen Bonds and Leading to Highly Strained Rings

Halides, Pseudo-Halides and Azides (1995)

  1. Mark S. Baird1,
  2. Ivan G. Bolesov2

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0023

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Baird, M. S. and Bolesov, I. G. 2009. Eliminations Involving Carbon–Halogen Bonds and Leading to Highly Strained Rings. Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    University of Wales, Department of Chemistry, Bangor, Wales, UK

  2. 2

    Moscow State University, Department of Chemistry, Moscow, Russia

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Dehydrohalogenations of Halogenated Cyclopropanes
  • 2
    Elimination of Halogen
  • 3
    1,2-Elimination of a Trialkylsilylhalide
  • 4
    Eliminations Leading to Cyclopropa-Aromatics
  • 5
    1,1- and 1,3-Elimination Leading to Cyclopropenes
  • 6
    1,3-Dehalogenation of 1-Halo-2-Halomethylcyclopropanes
  • 7
    Eliminations Leading to Bicyclo[1.1.0]but-1(3)-enes
  • 8
    1,2- and 1,3-Eliminations in Quadricyclanes
  • 9
    Dehalogenation and Dehydrohalogenation of Halogenated Cyclopropenes

Keywords:

  • dehydrohalogenations of halogenated cyclopropanes;
  • halogen elimination;
  • eliminations involving carbon–halogen bonds;
  • gas phase dehalogenations;
  • dehalosilylation;
  • gas phase elimination;
  • bicyclopropene and spiropentadine preparation;
  • eliminations leading to cyclopropa-aromatics

Featured Compounds

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  1. 1 - 97
Compound 1
Molecular Weight:200.748
Molecular Formula:C12H21Cl
InChIKey:SBMRDOFARHPHAK-BQYQJAHWSA-N
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Compound 2
Molecular Weight:238.4088
Molecular Formula:C16H30O
InChIKey:SKFUMYHUESYOAS-HRFIDBLHSA-N
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Compound 3
Molecular Weight:140.61
Molecular Formula:C8H9Cl
InChIKey:KFLSKRYMQSOYQB-UHFFFAOYSA-N
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Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 6
Molecular Weight:183.045
Molecular Formula:C8H7Br
InChIKey:AVNHTFUWAOAZBN-UHFFFAOYSA-N
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 8
Molecular Weight:372.522
Molecular Formula:C25H24OS
InChIKey:MPXZDDSFVFLHHF-UHFFFAOYSA-N
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Compound 10
Molecular Weight:66.1011
Molecular Formula:C5H6
InChIKey:CIRQLHNCULZPSO-UHFFFAOYSA-N
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Compound 9
Molecular Weight:137.007
Molecular Formula:C5H6Cl2
InChIKey:MXRGPDJKKHTJID-UHFFFAOYSA-N
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Compound 97
Molecular Weight:148.2447
Molecular Formula:C11H16
InChIKey:KZQXSYBZCHNSOL-UHFFFAOYSA-N
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Compound 11
Molecular Weight:102.562
Molecular Formula:C5H7Cl
InChIKey:XDEMBFVACUSZAE-UHFFFAOYSA-N
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Compound 12
Molecular Weight:102.562
Molecular Formula:C5H7Cl
InChIKey:XDEMBFVACUSZAE-UHFFFAOYSA-N
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Compound 13
Molecular Weight:122.981
Molecular Formula:C4H4Cl2
InChIKey:ZXJLSJGRBYTJTQ-UHFFFAOYSA-N
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Compound 14
Molecular Weight:293.188
Molecular Formula:C16H14Cl2O
InChIKey:IJXVLOWYNJWFCL-UHFFFAOYSA-N
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Compound 15
Molecular Weight:217.092
Molecular Formula:C10H10Cl2O
InChIKey:VMULMYLBHGTPIO-UHFFFAOYSA-N
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Compound 16
Molecular Weight:414.4945
Molecular Formula:C30H22O2
InChIKey:NDJFRCUTBISPCX-UHFFFAOYSA-N
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Compound 16a
Molecular Weight:450.955
Molecular Formula:C30H23ClO2
InChIKey:STUIFPILIVHNAN-UHFFFAOYSA-N
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Compound 17
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 18
Molecular Weight:Not Available
Molecular Formula:(CH2)nC3H2Cl2
InChIKey:KHBWTHBCRNBNRW-UHFFFAOYSA-N
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Compound 19
Molecular Weight:Not Available
Molecular Formula:(CH2)nC3HCl
InChIKey:RRSGTIFKBDQFDK-UHFFFAOYSA-N
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Compound 61
Molecular Weight:Not Available
Molecular Formula:(CH2)nC3HCl
InChIKey:RRSGTIFKBDQFDK-UHFFFAOYSA-N
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Compound 20
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:XNXGTVDICCSLJB-UHFFFAOYSA-N
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Compound 21
Molecular Weight:114.573
Molecular Formula:C6H7Cl
InChIKey:BUAKPITZELZWNI-UHFFFAOYSA-N
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Compound 22
Molecular Weight:153.007
Molecular Formula:C5H6Cl2O
InChIKey:CBHYXIPIDCRLQN-UHFFFAOYSA-N
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Compound 23
Molecular Weight:116.546
Molecular Formula:C5H5ClO
InChIKey:WKQQPZIDNCTOFY-UHFFFAOYSA-N
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Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 25
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 26
Molecular Weight:169.072
Molecular Formula:C5H6Cl2S
InChIKey:KWZKYKTYAGIMSM-UHFFFAOYSA-N
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Compound 27
Molecular Weight:132.611
Molecular Formula:C5H5ClS
InChIKey:WSOUTIBMHPHLLB-UHFFFAOYSA-N
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Compound 28
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H5Cl3
InChIKey:VXSYGPXSTXEFJN-UHFFFAOYSA-N
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Compound 34
Molecular Weight:146.2289
Molecular Formula:C11H14
InChIKey:MLUWUPGLWNWIHU-UHFFFAOYSA-N
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Compound 29
Molecular Weight:168.663
Molecular Formula:C10H13Cl
InChIKey:OIMPDEASXXESJQ-UHFFFAOYSA-N
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Compound 30
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:SKFNAJLVICRCJJ-UHFFFAOYSA-N
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Compound 31
Molecular Weight:167.656
Molecular Formula:C10H13Cl
InChIKey:YIYLPBVSFOLELZ-UHFFFAOYSA-N
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Compound 32
Molecular Weight:168.663
Molecular Formula:C10H13Cl
InChIKey:OIMPDEASXXESJQ-UHFFFAOYSA-N
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Compound 33
Molecular Weight:182.69
Molecular Formula:C11H15Cl
InChIKey:KFKFWAVOAAWRHB-UHFFFAOYSA-N
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Compound 35
Molecular Weight:182.69
Molecular Formula:C11H15Cl
InChIKey:KFKFWAVOAAWRHB-UHFFFAOYSA-N
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Compound 36
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37
Molecular Weight:142.1971
Molecular Formula:C11H10
InChIKey:OORRQYZWSVJKSO-UHFFFAOYSA-N
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Compound 38
Molecular Weight:142.1971
Molecular Formula:C11H10
InChIKey:RVJUDUADOMIBMH-UHFFFAOYSA-N
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Compound 39
Molecular Weight:142.1971
Molecular Formula:C11H10
InChIKey:XHVULKQHRQZNMW-UHFFFAOYSA-N
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Compound 40
Molecular Weight:225.125
Molecular Formula:C11H13Br
InChIKey:SLRVWZFCKUQXGR-UHFFFAOYSA-N
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Compound 41
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 42
Molecular Weight:298.036
Molecular Formula:C12H12Cl4
InChIKey:NSSPACYUNDYPLU-UHFFFAOYSA-N
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Compound 43
Molecular Weight:188.653
Molecular Formula:C12H9Cl
InChIKey:QPNBLTAZSMWHID-UHFFFAOYSA-N
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Compound 44
Molecular Weight:203.108
Molecular Formula:C10H12Cl2
InChIKey:DXCJHPIFXOILHR-UHFFFAOYSA-N
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Compound 45
Molecular Weight:166.647
Molecular Formula:C10H11Cl
InChIKey:VGQRDAADNWXUMI-UHFFFAOYSA-N
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Compound 46
Molecular Weight:483.881
Molecular Formula:C14H14Br2Cl4
InChIKey:XOFMWMYYCVEINR-UHFFFAOYSA-N
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Compound 47
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:XTIYGYYNVWOBAT-UHFFFAOYSA-N
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Compound 48
Molecular Weight:253.167
Molecular Formula:C14H14Cl2
InChIKey:SAGUHRROIYSUQV-UHFFFAOYSA-N
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Compound 49
Molecular Weight:253.167
Molecular Formula:C14H14Cl2
InChIKey:GCNPZQVBMJRLPL-UHFFFAOYSA-N
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Compound 50
Molecular Weight:326.089
Molecular Formula:C14H16Cl4
InChIKey:QRFSJMGQKYHZCI-UHFFFAOYSA-N
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Compound 51
Molecular Weight:253.167
Molecular Formula:C14H14Cl2
InChIKey:SAGUHRROIYSUQV-UHFFFAOYSA-N
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Compound 53
Molecular Weight:216.706
Molecular Formula:C14H13Cl
InChIKey:PKJVGRDGTGEKIO-UHFFFAOYSA-N
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Compound 54
Molecular Weight:308.4986
Molecular Formula:C20H36O2
InChIKey:CMRNMZJAUFXOQF-UHFFFAOYSA-N
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Compound 55
Molecular Weight:324.498
Molecular Formula:C20H36O3
InChIKey:WXALBAWIQGNQSQ-UHFFFAOYSA-N
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Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 57
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 58
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 60
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H10Cl2Si
InChIKey:VAXVCDKXZMRNTD-UHFFFAOYSA-N
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Compound 62
Molecular Weight:114.573
Molecular Formula:C6H7Cl
InChIKey:BUAKPITZELZWNI-UHFFFAOYSA-N
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Compound 63
Molecular Weight:165.06
Molecular Formula:C7H10Cl2
InChIKey:HHPTYVGXBCTKTF-AATRIKPKSA-N
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Compound 64
Molecular Weight:128.599
Molecular Formula:C7H9Cl
InChIKey:PZCCSJYFXQXAST-UHFFFAOYSA-N
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Compound 65
Molecular Weight:128.599
Molecular Formula:C7H9Cl
InChIKey:WCEXMFVIUDRXKR-UHFFFAOYSA-N
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Compound 66
Molecular Weight:128.599
Molecular Formula:C7H9Cl
InChIKey:DJWRLOGSCWTZTQ-VOTSOKGWSA-N
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Compound 67
Molecular Weight:295.396
Molecular Formula:C12H24Cl2Si2
InChIKey:JDOSHUTTXVDUPU-UHFFFAOYSA-N
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Compound 68
Molecular Weight:186.754
Molecular Formula:C9H15ClSi
InChIKey:VRTJHTFWUSMBKM-SREVYHEPSA-N
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Compound 69
Molecular Weight:163.044
Molecular Formula:C7H8Cl2
InChIKey:YTIQWGNUAAQUSP-UHFFFAOYSA-N
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Compound 70
Molecular Weight:396.908
Molecular Formula:C27H21ClO
InChIKey:OQZXLHNAQRQCSV-UHFFFAOYSA-N
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Compound 71
Molecular Weight:234.943
Molecular Formula:C7H8Cl4
InChIKey:RKJTXSSXUHEQHV-XFMUEVFYSA-N
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Compound 72
Molecular Weight:323.845
Molecular Formula:C7H8Br2Cl2
InChIKey:JBVBJSLRJUNMTQ-XFMUEVFYSA-N
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Compound 74
Molecular Weight:140.1812
Molecular Formula:C11H8
InChIKey:SHKRKDNBUOUWRB-UHFFFAOYSA-N
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Compound 73
Molecular Weight:286.027
Molecular Formula:C7H10Br2S
InChIKey:AFOUOJCRMIELQP-UHFFFAOYSA-N
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Compound 75
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 76
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 77
Molecular Weight:346.885
Molecular Formula:C8H11Br3
InChIKey:PWZQQDWYIHYJHJ-HUDPQJTASA-N
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Compound 78
Molecular Weight:332.848
Molecular Formula:C7H9Br3
InChIKey:KUUHOQBIKZPHCG-XRVVJQKQSA-N
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Compound 79
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 80
Molecular Weight:195.485
Molecular Formula:C6H8BrCl
InChIKey:QISCKKWXCDPVFE-UHFFFAOYSA-N
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Compound 81
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 82
Molecular Weight:296.815
Molecular Formula:C5H6Br2Cl2
InChIKey:RCRVZCIUKQNOIS-UHFFFAOYSA-N
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Compound 83
Molecular Weight:319.9101
Molecular Formula:C5H6I2
InChIKey:JJWNAOGSAYBEPB-UHFFFAOYSA-N
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Compound 84
Molecular Weight:225.909
Molecular Formula:C5H6Br2
InChIKey:BSHLUOAVMJBIHU-UHFFFAOYSA-N
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Compound 85
Molecular Weight:166.973
Molecular Formula:C6H8BrLi
InChIKey:WVBXWFYAVWACES-UHFFFAOYSA-N
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Compound 86
Molecular Weight:270.3676
Molecular Formula:C21H18
InChIKey:NTFGVIMWNMHHGB-UHFFFAOYSA-N
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Compound 88
Molecular Weight:270.3676
Molecular Formula:C21H18
InChIKey:BZUKISUWBNPYFI-UHFFFAOYSA-N
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Compound 89
Molecular Weight:184.2768
Molecular Formula:C14H16
InChIKey:NGARRWVZELQVCW-UHFFFAOYSA-N
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Compound 90
Molecular Weight:126.583
Molecular Formula:C7H7Cl
InChIKey:OPAKWBZYURQTGD-UHFFFAOYSA-N
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Compound 91
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 92
Molecular Weight:126.583
Molecular Formula:C7H7Cl
InChIKey:WTGKLSWCVBNZNH-UHFFFAOYSA-N
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Compound 93
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 94
Molecular Weight:174.282
Molecular Formula:C13H18
InChIKey:FJPJDKKUCYMVKJ-UHFFFAOYSA-N
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Compound 95
Molecular Weight:116.1598
Molecular Formula:C9H8
InChIKey:RMNWVOOQJCJESL-UHFFFAOYSA-N
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Compound 96
Molecular Weight:231.517
Molecular Formula:C9H8BrCl
InChIKey:SKRFHNLSKBWEEB-UHFFFAOYSA-N
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Compound 98
Molecular Weight:219.151
Molecular Formula:C11H16Cl2
InChIKey:UUPDOKKQMUDIQL-UHFFFAOYSA-N
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Compound 99
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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  1. 1 - 97