Standard Article

1,2-Dioxatrisulfane (thiaperoxide) intermediates in type I and II photooxygenation reactions

Peroxides (2014)

  1. EDWARD L. CLENNAN

Published Online: 28 APR 2014

DOI: 10.1002/9780470682531.pat0876

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

CLENNAN, E. L. 2014. 1,2-Dioxatrisulfane (thiaperoxide) intermediates in type I and II photooxygenation reactions. Patai's Chemistry of Functional Groups. 1–34.

Author Information

  1. Department of Chemistry, University of Wyoming, Laramie, WY 82071, USA

Publication History

  1. Published Online: 28 APR 2014

Chemistry Terms

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Abstract

This review focuses on a discussion of labile metastable sulfur-based peroxides (persulfoxides-R2S+OO; 3-membered S[BOND]O[BOND]O ring thiadioxiranes-c-R2SO2; hydroperoxy sulfonium ylides-R(R′CH[BOND])S+OO; and, peroxy sulfuranes-R2S(OR′)OOR′′) that have been observed or implicated in Type I and II photooxygenation reactions. Evidence for formation and computational structures of these novel intermediates is presented.

Keywords:

  • persulfoxide;
  • thiadioxirane;
  • hydroperoxy sulfonium ylide;
  • peroxy sulfuranes;
  • singlet oxygen

Featured Compounds

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  1. 1 - 55
Compound 37
Molecular Weight:104.171
Molecular Formula:C4H8OS
InChIKey:HNXMKNMCALMEPP-UHFFFAOYSA-N
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Compound 12
Molecular Weight:224.393
Molecular Formula:C8H20O3SSi
InChIKey:MZCDEBHYPZEFRO-UHFFFAOYSA-N
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Compound 17
Molecular Weight:225.307
Molecular Formula:C11H15NO2S
InChIKey:OGSLIBJTCUFSBS-UHFFFAOYSA-N
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Compound 23
Molecular Weight:192.32
Molecular Formula:C12H16S
InChIKey:YWDRRSHEQGWEBD-UHFFFAOYSA-N
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Compound 27
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 21
Molecular Weight:200.299
Molecular Formula:C13H12S
InChIKey:LKMCJXXOBRCATQ-UHFFFAOYSA-N
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Compound 14
Molecular Weight:208.394
Molecular Formula:C8H20O2SSi
InChIKey:IAKMAKILMLRZRD-UHFFFAOYSA-N
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Compound 29a
Molecular Weight:99.164
Molecular Formula:C2H6O2S
InChIKey:Not Available
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Compound 29b
Molecular Weight:100.17
Molecular Formula:C2H6O2S
InChIKey:Not Available
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Compound 4
Molecular Weight:347.209
Molecular Formula:C14H28N2NiS2
InChIKey:DBXIFEQHQNUIKQ-UHFFFAOYSA-L
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Compound 46
Molecular Weight:253.372
Molecular Formula:C14H20O2S
InChIKey:ZHNDIBOHUVIVIH-UHFFFAOYSA-N
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Compound 6
Molecular Weight:142.262
Molecular Formula:C8H14S
InChIKey:DVLYDJRYYXRYGD-UHFFFAOYSA-N
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Compound 28
Molecular Weight:84.17
Molecular Formula:C2H6OS
InChIKey:Not Available
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Compound 36
Molecular Weight:140.632
Molecular Formula:C4H9ClOS
InChIKey:LIPRCTSGLFLUNJ-UHFFFAOYSA-N
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Compound 39
Molecular Weight:154.228
Molecular Formula:C5H14O3S
InChIKey:GZQFGGJRIWGMBG-UHFFFAOYSA-N
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Compound 40
Molecular Weight:126.175
Molecular Formula:C3H10O3S
InChIKey:AWUKYULOYDKBHK-UHFFFAOYSA-N
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Compound 19
Molecular Weight:89.179
Molecular Formula:C4H8S
InChIKey:RAOIDOHSFRTOEL-UHFFFAOYSA-O
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Compound 18
Molecular Weight:243.28
Molecular Formula:C10H13NO4S
InChIKey:FIYKNXNABXYULU-UHFFFAOYSA-N
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Compound 43
Molecular Weight:239.389
Molecular Formula:C14H22OS
InChIKey:UMYQKLAJOWMIKW-UHFFFAOYSA-N
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Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1
Molecular Weight:74.145
Molecular Formula:C3H6S
InChIKey:MBNVSWHUJDDZRH-VKHMYHEASA-N
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Compound DCA
Molecular Weight:228.2481
Molecular Formula:C16H8N2
InChIKey:BIOPPFDHKHWJIA-UHFFFAOYSA-N
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Compound 3
Molecular Weight:443.451
Molecular Formula:C12H12N2PtS2
InChIKey:LYJYJMXLASLORR-UHFFFAOYSA-L
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Compound 44
Molecular Weight:255.388
Molecular Formula:C14H22O2S
InChIKey:GPEGBEJGTKGSPF-UHFFFAOYSA-N
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Compound 10
Molecular Weight:122.186
Molecular Formula:C4H10O2S
InChIKey:YTBFKEQSNOQHRG-UHFFFAOYSA-N
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Compound 9SO
Molecular Weight:164.289
Molecular Formula:C6H12OS2
InChIKey:GWVZKOUSJKSZQM-UHFFFAOYSA-N
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Compound A
Molecular Weight:168.314
Molecular Formula:C6H12OS2
InChIKey:Not Available
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Compound B
Molecular Weight:168.314
Molecular Formula:C6H12OS2
InChIKey:Not Available
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Compound 31
Molecular Weight:254.302
Molecular Formula:C12H14O4S
InChIKey:HUKZMANDYPEGAU-POHAHGRESA-N
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Compound 32
Molecular Weight:254.302
Molecular Formula:C12H14O4S
InChIKey:HUKZMANDYPEGAU-UXBLZVDNSA-N
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Compound 41
Molecular Weight:240.383
Molecular Formula:C9H20O3S2
InChIKey:VWTQLQJRXNLCLI-UHFFFAOYSA-N
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Compound A
Molecular Weight:156.631
Molecular Formula:C4H9ClO2S
InChIKey:ZTHAOOSTDKCPBR-UHFFFAOYSA-N
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Compound 42
Molecular Weight:212.33
Molecular Formula:C7H16O3S2
InChIKey:KAXAKZDEJNEOFR-UHFFFAOYSA-N
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Compound 20
Molecular Weight:102.198
Molecular Formula:C5H10S
InChIKey:YPWFISCTZQNZAU-UHFFFAOYSA-N
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Compound 45
Molecular Weight:271.387
Molecular Formula:C14H22O3S
InChIKey:PDDVZUKQMDQUJG-CQSZACIVSA-N
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Compound 13
Molecular Weight:224.393
Molecular Formula:C8H20O3SSi
InChIKey:KPAIDVVVKDKSMZ-UHFFFAOYSA-N
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Compound 26
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2
Molecular Weight:120.236
Molecular Formula:C4H8S2
InChIKey:LOZWAPSEEHRYPG-UHFFFAOYSA-N
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Compound B
Molecular Weight:156.631
Molecular Formula:C4H9ClO2S
InChIKey:AMXJYYISHZHNPS-UHFFFAOYSA-N
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Compound 8
Molecular Weight:209.308
Molecular Formula:C11H15NOS
InChIKey:KCZPTSSMXGSESL-UHFFFAOYSA-N
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Compound 51
Molecular Weight:244.375
Molecular Formula:C14H12S2
InChIKey:NLBUXLXRJPNORI-UHFFFAOYSA-N
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Compound 33
Molecular Weight:442.634
Molecular Formula:C16H26O6S4
InChIKey:XRPXJTFMCPYXCJ-GWQLSQFXSA-N
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Compound 7
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:XYYJMADPFXZNGP-UHFFFAOYSA-N
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Compound 9
Molecular Weight:148.289
Molecular Formula:C6H12S2
InChIKey:QQMWBFKOHYFXKQ-UHFFFAOYSA-N
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Compound 9SOSO
Molecular Weight:180.288
Molecular Formula:C6H12O2S2
InChIKey:AATMTGAOEOQVGO-UHFFFAOYSA-N
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Compound 11
Molecular Weight:192.394
Molecular Formula:C8H20OSSi
InChIKey:JKAWCQYPBJFWQL-UHFFFAOYSA-N
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Compound 49
Molecular Weight:Not Available
Molecular Formula:(CH2)nC7H8OS
InChIKey:YVRNRVQCHUBSGU-UHFFFAOYSA-N
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Compound 38
Molecular Weight:154.228
Molecular Formula:C5H14O3S
InChIKey:YKWVVCDVYHBACI-UHFFFAOYSA-N
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Compound 5
Molecular Weight:134.263
Molecular Formula:C5H10S2
InChIKey:WUWLIHSSYRWCQE-UHFFFAOYSA-N
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Compound 16
Molecular Weight:180.288
Molecular Formula:C6H12O2S2
InChIKey:BFAWVOZHVOZNTJ-UHFFFAOYSA-N
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Compound 47
Molecular Weight:253.372
Molecular Formula:C14H20O2S
InChIKey:ZHNDIBOHUVIVIH-UHFFFAOYSA-N
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Compound 48
Molecular Weight:253.372
Molecular Formula:C14H20O2S
InChIKey:ZHNDIBOHUVIVIH-UHFFFAOYSA-N
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Compound 15
Molecular Weight:74.145
Molecular Formula:C3H6S
InChIKey:XSROQCDVUIHRSI-UHFFFAOYSA-N
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Compound 30
Molecular Weight:222.303
Molecular Formula:C12H14O2S
InChIKey:UKLKTERIBQZCDQ-RMKNXTFCSA-N
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