Standard Article

Contemporary Trends in Dioxetane Chemistry

Peroxides (2006)

  1. Waldemar Adam1,2,
  2. Alexei V. Trofimov3,4

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0361

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Adam, W. and Trofimov, A. V. 2009. Contemporary Trends in Dioxetane Chemistry . Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    University of Würzburg, Institute of Organic Chemistry, Würzburg, Germany

  2. 2

    University of Puerto Rico, Department of Chemistry, Rio Piedras, Puerto Rico, USA

  3. 3

    Russian Academy of Sciences, Institute of Biochemical Physics, Moscow, Russian Federation

  4. 4

    University of Würzburg, Institute of Organic Chemistry, Würzburg, Germany

Publication History

  1. Published Online: 15 DEC 2009

Chemistry Terms

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Abstract

  • 1
    Introduction
  • 2
    Stereoselective Synthesis of Chiral Dioxetanes and their Transformations
  • 3
    α-Peroxy Lactone as Oxidant
  • 4
    Chemiluminescent Decomposition of 1,2-Dioxetanes
  • 5
    Bioanalytical Application of the Dioxetane Chemiluminescence
  • 6
    Photooxidation of DNA by 1,2-Dioxetanes
  • 7
    Conclusions
  • 8
    Acknowledgment

Keywords:

  • dioxetanes and dioxetanones - four-membered-ring cyclic peroxides;
  • chiral dioxetane stereoselective synthesis;
  • geminate chiral radical pair;
  • α-peroxy lactone as oxidant;
  • four-membered-ring cyclic congeners;
  • cleavage of 1,2-dioxetanes - model chemiluminescent process;
  • Chemically Initiated Electron-exchange Luminescence (CIEEL);
  • DNA and 1,2-dioxetane photooxidation

Featured Compounds

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  1. 1 - 61
Compound 1a
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:XHSOZGASJADGKU-FKBSVAGWSA-N
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Compound 1b
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:PTBXLHZPZGBORD-ICBDYAAISA-N
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Compound 1c
Molecular Weight:335.4394
Molecular Formula:C22H25NO2
InChIKey:ZLJBSEQHHRSVAH-DRPWZSEGSA-N
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Compound 3a
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:QTSSVEATYLZIEK-FPLPWBNLSA-N
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Compound 3b
Molecular Weight:266.3328
Molecular Formula:C15H22O4
InChIKey:CTTYPOBQDPWEQY-HJWRWDBZSA-N
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Compound 4
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:SPCASKIJCKGUAQ-UHFFFAOYSA-N
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Compound erythro-2a
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:RZJDGJXXINEQKN-RWHNRAKCSA-N
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Compound erythro-2b
Molecular Weight:266.3328
Molecular Formula:C15H22O4
InChIKey:NASGTPIBPLQKIL-BYLVEKLRSA-N
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Compound threo-2a
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:RZJDGJXXINEQKN-IBPAHSCNSA-N
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Compound threo-2b
Molecular Weight:266.3328
Molecular Formula:C15H22O4
InChIKey:NASGTPIBPLQKIL-SBESVPKRSA-N
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Compound erythro-1a
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:XHSOZGASJADGKU-BTOXTNAGSA-N
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Compound threo-1a
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:XHSOZGASJADGKU-OIUFIDJCSA-N
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Compound 2c
Molecular Weight:367.4382
Molecular Formula:C22H25NO4
InChIKey:AEIRATTYEXOCKA-BTVZNNDGSA-N
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Compound 5
Molecular Weight:242.3129
Molecular Formula:C16H18O2
InChIKey:QMYKDTSAEXOHCB-VYIIXAMBSA-N
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Compound 6
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 7
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:MHUUEDKTLIMBPS-UHFFFAOYSA-N
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Compound 8
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:118.1311
Molecular Formula:C5H10O3
InChIKey:BKBZFJRHYSCZQA-UHFFFAOYSA-N
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Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound m-15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound p-15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 15a
Molecular Weight:416.6257
Molecular Formula:C24H36O4Si
InChIKey:LRZSXBNWDXTNDF-UHFFFAOYSA-N
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Compound 15b
Molecular Weight:392.6043
Molecular Formula:C22H36O4Si
InChIKey:JMIMQIMHCUNUIF-UHFFFAOYSA-N
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Compound 17a
Molecular Weight:151.1399
Molecular Formula:C8H8O3
InChIKey:YKUCHDXIBAQWSF-UHFFFAOYSA-M
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Compound 17b
Molecular Weight:277.3361
Molecular Formula:C16H22O4
InChIKey:KLXXFCCQNSVIHT-UHFFFAOYSA-M
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Compound m-17
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound p-17
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound m-16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound p-16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 18
Molecular Weight:88.019
Molecular Formula:C2O4
InChIKey:WYNZXNXFHYJUTE-UHFFFAOYSA-N
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Compound 19
Molecular Weight:300.4351
Molecular Formula:C20H28O2
InChIKey:OLJVAWRLTPGYQL-UHFFFAOYSA-N
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Compound 15c
Molecular Weight:380.33
Molecular Formula:C18H23O7P
InChIKey:XYIPYISRNJUPBA-UHFFFAOYSA-L
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Compound 15d
Molecular Weight:464.5055
Molecular Formula:C24H32O9
InChIKey:CIZHYMVIFTYLLD-DVPTUDLWSA-N
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Compound 15e
Molecular Weight:301.3575
Molecular Formula:C18H22O4
InChIKey:RVRTXMFVLYHVQX-UHFFFAOYSA-M
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Compound CSPD
Molecular Weight:414.775
Molecular Formula:C18H22ClO7P
InChIKey:QWXOJIDBSHLIFI-UHFFFAOYSA-L
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Compound CDP
Molecular Weight:449.22
Molecular Formula:C18H21Cl2O7P
InChIKey:BGWCVNQUOXXBIM-UHFFFAOYSA-L
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Compound CDP-Star
Molecular Weight:449.22
Molecular Formula:C18H21Cl2O7P
InChIKey:AGMXMWDSGUBNPT-UHFFFAOYSA-L
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Compound BZPD
Molecular Weight:513.5
Molecular Formula:C25H26NO7PS
InChIKey:WQCHHPPYADAQSR-UHFFFAOYSA-L
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Compound 21a
Molecular Weight:418.6416
Molecular Formula:C24H38O4Si
InChIKey:JCRHYHVWFVCQDZ-UHFFFAOYSA-N
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Compound 21b
Molecular Weight:418.6416
Molecular Formula:C24H38O4Si
InChIKey:GLOWKEFIZUBFRR-UHFFFAOYSA-N
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Compound 21c
Molecular Weight:418.6416
Molecular Formula:C24H38O4Si
InChIKey:DZPPVAFDWDCUCS-UHFFFAOYSA-N
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Compound 21d
Molecular Weight:434.707
Molecular Formula:C24H38O3SSi
InChIKey:ZZLVTLDSQNOVGK-UHFFFAOYSA-N
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Compound 21e
Molecular Weight:434.707
Molecular Formula:C24H38O3SSi
InChIKey:GTSISBBIOKTVCY-UHFFFAOYSA-N
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Compound 21f
Molecular Weight:434.707
Molecular Formula:C24H38O3SSi
InChIKey:KMXBCFQNINTOHS-UHFFFAOYSA-N
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Compound 22a
Molecular Weight:413.3876
Molecular Formula:C20H22F3NO5
InChIKey:NDKMBQWCNFXGKY-UHFFFAOYSA-N
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Compound 22b
Molecular Weight:345.3896
Molecular Formula:C19H23NO5
InChIKey:YFSTWWYJXVWTSW-UHFFFAOYSA-N
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Compound 22c
Molecular Weight:401.4959
Molecular Formula:C23H31NO5
InChIKey:ZAKSQWIYKXHACH-UHFFFAOYSA-N
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Compound 8-oxodGuo
Molecular Weight:282.2527
Molecular Formula:C11H14N4O5
InChIKey:RRXWHQZSIDTACH-SHYZEUOFSA-N
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Compound 4-HO-8-oxodGuo
Molecular Weight:298.2521
Molecular Formula:C11H14N4O6
InChIKey:YNRCDCRQTDKPGI-GWLYMAACSA-N
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Compound dGuo
Molecular Weight:266.2533
Molecular Formula:C11H14N4O4
InChIKey:CZFUQKNOFZPABS-LKEWCRSYSA-N
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Compound 23a
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:JQVQHBAHURDRSY-UHFFFAOYSA-N
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Compound 23b
Molecular Weight:146.1843
Molecular Formula:C7H14O3
InChIKey:VPFOZRDBBCBSSD-UHFFFAOYSA-N
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Compound 23c
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:DCAFHRPDWWMZAZ-UHFFFAOYSA-N
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Compound 24
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:ZWVHTXAYIKBMEE-UHFFFAOYSA-N
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Compound 25
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:ZXTYSCUYFKXAPA-UHFFFAOYSA-N
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  1. 1 - 61