Standard Article

Stereochemical Aspects—Conformation and Configuration

Cyclobutanes (2005)

  1. Ulf Berg

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0317

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Berg, U. 2009. Stereochemical Aspects—Conformation and Configuration. Patai's Chemistry of Functional Groups. .

Author Information

  1. Lund University, Organic Chemistry 1, Department of Chemistry, Lund, Sweden

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction
  • 2
    Conformation
  • 3
    Resolution and Determination of Configuration
  • 4
    Cyclobutane in Bicyclic Systems
  • 5
    Cyclobutane in Polycyclic Systems
  • 6
    Stereochemistry Of Ring Closure and Ring-Opening Reactions
  • 7
    Natural Products

Keywords:

  • stereochemical aspects of cyclobutane and its derivatives;
  • conformation of cyclobutane;
  • H NMR Karplus-type relations and molecular mechanics;
  • orbital correlation diagram for cyclobutane;
  • photodimer formation from cinnamic amide;
  • ring closure and ring-opening reaction stereochemistry;
  • cyclobutane ring and biological activity;
  • torsional equilibration

Featured Compounds

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  1. 1 - 88
Compound 29
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:TXWRERCHRDBNLG-UHFFFAOYSA-N
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Compound 2
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:UCZTUROBDISEKY-UHFFFAOYSA-N
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Compound 3
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:VYQSEHNZACAPGH-UHFFFAOYSA-N
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Compound 4
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:PXEFRHXCZUHQRZ-UHFFFAOYSA-N
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Compound 5
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:NVNHBPOLPPDKRC-UHFFFAOYSA-N
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Compound 6
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:DENCHDMOLAALHN-UHFFFAOYSA-N
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Compound 7
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:YAIGILBWPZYHJE-UHFFFAOYSA-N
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Compound 8
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:WZVDQPYGHWVMGO-UHFFFAOYSA-N
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Compound 9
Molecular Weight:160.2554
Molecular Formula:C12H16
InChIKey:XXHDHKZTASMVSX-HUVAQWKNSA-N
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Compound 10
Molecular Weight:296.3172
Molecular Formula:C18H16O4
InChIKey:QWFRRFLKWRIKSZ-UHFFFAOYSA-N
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Compound 11
Molecular Weight:296.3172
Molecular Formula:C18H16O4
InChIKey:QVNDSQQNODQYJM-UHFFFAOYSA-N
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Compound 12
Molecular Weight:558.6662
Molecular Formula:C36H34N2O4
InChIKey:KQMQOKPPAJOIAB-QBUDEFGCSA-N
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Compound 13
Molecular Weight:279.3331
Molecular Formula:C18H17NO2
InChIKey:IIGLEDAFGCMQAJ-XBLVEGMJSA-N
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Compound 14
Molecular Weight:108.542
Molecular Formula:C4H6ClF
InChIKey:JEKSYLNKTQNPOC-UHFFFAOYSA-N
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Compound 15
Molecular Weight:144.523
Molecular Formula:C4H4ClF3
InChIKey:ZZQYDYODFHABLC-VKHMYHEASA-N
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Compound 77
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:GRWFGVWFFZKLTI-UHFFFAOYSA-N
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Compound 16
Molecular Weight:292.2855
Molecular Formula:C18H12O4
InChIKey:LLDOJHIQWQQUIQ-VGWMRTNUSA-N
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Compound 17
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17b
Molecular Weight:352.3374
Molecular Formula:C20H16O6
InChIKey:MIJSHCHHDUDNBB-MLHJIOFPSA-N
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Compound 18
Molecular Weight:434.5305
Molecular Formula:C32H22N2
InChIKey:JVVQSMGYPOGWIO-KJHMZRPRSA-N
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Compound 17a
Molecular Weight:292.2855
Molecular Formula:C18H12O4
InChIKey:NEAHZKVDPWZHGT-JJXSEGSLSA-N
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Compound 20
Molecular Weight:324.3704
Molecular Formula:C20H20O4
InChIKey:YQBHKNAHPIEGIK-CALCHBBNSA-N
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Compound 21
Molecular Weight:264.0788
Molecular Formula:C7H2F6O4
InChIKey:PXEGAJFWOFNGLE-UHFFFAOYSA-N
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Compound 22
Molecular Weight:111.1191
Molecular Formula:C6H8O2
InChIKey:ORCXPYPDHLVQFP-UHFFFAOYSA-M
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Compound 23
Molecular Weight:196.4045
Molecular Formula:C12H24Si
InChIKey:VXPITLOQIBCTTN-UHFFFAOYSA-N
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Compound 24
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:MHLPKAGDPWUOOT-SYDPRGILSA-N
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Compound 25
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:UCZTUROBDISEKY-OCAPTIKFSA-N
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Compound 26
Molecular Weight:190.3245
Molecular Formula:C14H22
InChIKey:PWSQENPNAXIRAU-UHFFFAOYSA-N
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Compound 27
Molecular Weight:90.1225
Molecular Formula:C7H6
InChIKey:VPKOBODOQYIIJE-UHFFFAOYSA-N
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Compound 30
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 31
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:YMAGFSBMYVGYKC-UHFFFAOYSA-N
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Compound 32
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:YZSBTFGLXJUHBJ-XGPRVQHZSA-N
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Compound 33
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:JQZAKMJZYGPUFD-WATHFIQWSA-N
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Compound 34
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:VLPXMVRWCPGDPP-WATHFIQWSA-N
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Compound 35
Molecular Weight:152.2765
Molecular Formula:C11H20
InChIKey:BBTXFDSETOQPGS-UHFFFAOYSA-N
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Compound 36
Molecular Weight:134.2182
Molecular Formula:C10H14
InChIKey:IIDCALDHTNAAEF-UHFFFAOYSA-N
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Compound 37
Molecular Weight:282.4629
Molecular Formula:C21H30
InChIKey:XPLOGWDEPLMXPW-UHFFFAOYSA-N
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Compound 38
Molecular Weight:310.5161
Molecular Formula:C23H34
InChIKey:BDPRKZJBKPCMTK-UHFFFAOYSA-N
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Compound 39
Molecular Weight:246.3016
Molecular Formula:C15H18O3
InChIKey:ZAMISBCFXGYXIE-UHFFFAOYSA-N
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Compound 40
Molecular Weight:298.4623
Molecular Formula:C21H30O
InChIKey:FUDQHFHTHUBDLN-UHFFFAOYSA-N
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Compound 41
Molecular Weight:86.1718
Molecular Formula:C6H12
InChIKey:Not Available
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Compound 42
Molecular Weight:86.1718
Molecular Formula:C6H12
InChIKey:Not Available
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Compound 43
Molecular Weight:86.1718
Molecular Formula:C6H12
InChIKey:Not Available
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Compound 44
Molecular Weight:186.253
Molecular Formula:C12H14N2
InChIKey:SOTXSEZFFFHBBQ-FEQGKNJQSA-N
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Compound 45
Molecular Weight:186.253
Molecular Formula:C12H14N2
InChIKey:MBJYTNYCTTXFAR-ZPUQHVIOSA-N
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Compound 46
Molecular Weight:260.3728
Molecular Formula:C20H20
InChIKey:YTDXIALIZRXIFD-BGYRXZFFSA-N
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Compound 47
Molecular Weight:260.3728
Molecular Formula:C20H20
InChIKey:OCSOURWVUKQNSH-UHFFFAOYSA-N
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Compound 48
Molecular Weight:260.3728
Molecular Formula:C20H20
InChIKey:OCSOURWVUKQNSH-UHFFFAOYSA-N
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Compound 49
Molecular Weight:260.3728
Molecular Formula:C20H20
InChIKey:OCSOURWVUKQNSH-UHFFFAOYSA-N
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Compound 50
Molecular Weight:264.4046
Molecular Formula:C20H24
InChIKey:UUXSSVRCYZWAFM-UHFFFAOYSA-N
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Compound 51
Molecular Weight:Not Available
Molecular Formula:(CH2)nC19H20O2
InChIKey:XWHNBZOWRPFHLI-IYBDPMFKSA-N
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Compound 52
Molecular Weight:Not Available
Molecular Formula:(CH2)nC19H22O2
InChIKey:FDHLNFVFMBCSGV-UHFFFAOYSA-N
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Compound 53
Molecular Weight:Not Available
Molecular Formula:(CH2)nC21H20
InChIKey:MVAULXXIAOZSCS-OBMJPTGESA-N
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Compound 54
Molecular Weight:Not Available
Molecular Formula:(CH2)nC24H26O2
InChIKey:ACWJYWGSKUBNKM-UHFFFAOYSA-N
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Compound 55
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:VDRBUVNLLKKVPW-UHFFFAOYSA-N
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Compound 56
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:BZYDIMMJKULPEZ-UHFFFAOYSA-N
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Compound 57
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:VYXHVRARDIDEHS-CDTWYVJESA-N
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Compound 58
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:YRPULDYFWXJQQE-UHFFFAOYSA-N
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Compound 59
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:DZSNJASVIURWOG-UHFFFAOYSA-N
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Compound 60
Molecular Weight:212.64
Molecular Formula:C9H12ClF3
InChIKey:TVUKDYLTCDPGCS-UHFFFAOYSA-N
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Compound 61
Molecular Weight:229.094
Molecular Formula:C9H12Cl2F2
InChIKey:JIHCZYKACLJBQY-UHFFFAOYSA-N
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Compound 62
Molecular Weight:149.2328
Molecular Formula:C10H15N
InChIKey:ZGZXMTWTSWWMQR-VIFPVBQESA-N
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Compound 63
Molecular Weight:84.1378
Molecular Formula:C5H9N
InChIKey:Not Available
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Compound 64
Molecular Weight:411.634
Molecular Formula:C16H12BrClN2O4
InChIKey:PANKSQVBNLSIHL-YHUYYLMFSA-N
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Compound 65
Molecular Weight:411.634
Molecular Formula:C16H12BrClN2O4
InChIKey:PANKSQVBNLSIHL-VGWMRTNUSA-N
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Compound 66
Molecular Weight:148.986
Molecular Formula:C4H5BrO
InChIKey:XQZZIZVMMMRELO-UHFFFAOYSA-N
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Compound 67
Molecular Weight:87.0954
Molecular Formula:C4H6O2
InChIKey:Not Available
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Compound 68
Molecular Weight:166.217
Molecular Formula:C10H14O2
InChIKey:DEJSRYLFYBCASZ-UHFFFAOYSA-N
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Compound 69
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:CXGDCGIPEJKSCK-UHFFFAOYSA-N
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Compound 70
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:SJKPJXGGNKMRPD-VHSXEESVSA-N
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Compound 71
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:SJKPJXGGNKMRPD-NXEZZACHSA-N
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Compound 72
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:XUCVWTVHEYSKFF-WDEREUQCSA-N
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Compound 73
Molecular Weight:410.5766
Molecular Formula:C21H34O6Si
InChIKey:GVUCQUSBHHLBIQ-MQEZQYLSSA-N
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Compound 75
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:DVAHCHCZPNEYNF-DTWKUNHWSA-N
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Compound 76
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:Not Available
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Compound 78
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:SIAMILUXHSYBMT-UHFFFAOYSA-N
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Compound 79
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:DSOHSNQLPOOWJO-WRMMETIMSA-N
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Compound 80
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:NPNUFJAVOOONJE-GFUGXAQUSA-N
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Compound 81
Molecular Weight:250.3334
Molecular Formula:C15H22O3
InChIKey:UJUDUTPSCRULOQ-QVPQWIHMSA-N
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Compound 82
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:FBSBGGJQVUYUDB-NJZAAPMLSA-N
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Compound 83
Molecular Weight:206.3669
Molecular Formula:C15H26
InChIKey:WAAMRUBBXSLLEE-SEWRKBRGSA-N
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Compound 84
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:BWAXOYJGXIEEOE-SQWANPQRSA-N
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Compound 85
Molecular Weight:378.143
Molecular Formula:C15H22Br2O
InChIKey:DZASHWYZXQVNJH-BSSFAIJFSA-N
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Compound 86
Molecular Weight:159.14
Molecular Formula:C6H9NO4
InChIKey:GGMYWPBNZXRMME-MYNUVTBMSA-N
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Compound 87
Molecular Weight:127.1412
Molecular Formula:C6H9NO2
InChIKey:XEVFXAFXZZYFSX-UHFFFAOYSA-N
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Compound 88
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:OZUDURPARMOLKB-UJURSFKZSA-N
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Compound 89
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:OZUDURPARMOLKB-INEUFUBQSA-N
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Compound 90
Molecular Weight:243.2994
Molecular Formula:C12H21NO4
InChIKey:AOJXKOSBUVHAIA-YUMQZZPRSA-N
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