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Selective oxidation of organic compounds using pyridinium-1-sulfonate fluorochromate, C5H5NSO3H [CrO3F] (PSFC)

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Abstract

Efficient selective oxidation of primary, secondary, and benzylic alcohols to the corresponding carbonyl compounds by a new chromium oxidizing reagent, pyridinium-1-sulfonate fluorochromate, C5H5NSO3H [CrO3F] (PSFC) is reported. Various cholesterol derivatives were easily converted to related oxocholesterol from allylic oxidation at lower temperature in comparison to other general oxidants. This oxidation procedure is simple and affords good yields.

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References

  • E Pratt J Van de Castle (1961) J Org Chem 26 2973 Occurrence Handle10.1021/jo01066a084 Occurrence Handle1:CAS:528:DyaF38XitV2k

    Article  CAS  Google Scholar 

  • S Regen C Koteel (1977) J Am Chem Soc 99 3837 Occurrence Handle10.1021/ja00453a053 Occurrence Handle1:CAS:528:DyaE2sXks1Onsbc%3D

    Article  CAS  Google Scholar 

  • Mukaiyama T, Matsuo J, Iida D, Kitagawa H (2001) Chem Lett: 846

  • J Tang J Zhu Z Shen Y Zhang (2007) Tetrahedron Lett 48 1919 Occurrence Handle10.1016/j.tetlet.2007.01.084 Occurrence Handle1:CAS:528:DC%2BD2sXhvVOrsLY%3D

    Article  CAS  Google Scholar 

  • J Collins W Hes F Frank (1968) Tetrahedron Lett 9 3363 Occurrence Handle10.1016/S0040-4039(00)89494-0

    Article  Google Scholar 

  • E Corey G Fleet (1973) Tetrahedron Lett 44 4499 Occurrence Handle10.1016/S0040-4039(01)87260-9

    Article  Google Scholar 

  • E Corey J Suggs (1975) Tetrahedron Lett 16 2647 Occurrence Handle10.1016/S0040-4039(00)75204-X

    Article  Google Scholar 

  • E Corey G Schmidt (1979) Tetrahedron Lett 20 399 Occurrence Handle10.1016/S0040-4039(01)93515-4

    Article  Google Scholar 

  • Guziece F, Luzzio F (1980) Synthesis: 691

  • M Bhattacherjee M Chaudhuri S Purkayastha (1987) Tetrahedron 43 5389 Occurrence Handle10.1016/S0040-4020(01)87719-X

    Article  Google Scholar 

  • MZ Kassaee AR Bekhradnia (2004) Phosphorus Sulfur 179 2025 Occurrence Handle10.1080/10426500490473555 Occurrence Handle1:CAS:528:DC%2BD2cXoslyktL4%3D

    Article  CAS  Google Scholar 

  • CO Wilson O Gisvold (1998) Textbook of organic medicinal and pharmaceutical chemistry Lippincott-Raven New York

    Google Scholar 

  • G Schroepfer SuffixJr (1981) Ann Rev Biochem 51 585 Occurrence Handle10.1146/annurev.bi.50.070181.003101

    Article  Google Scholar 

  • FR Taylor SE Saucier EP Shown EJ Parish AA Kandutsch (1984) J Biol Chem 259 12382 Occurrence Handle1:CAS:528:DyaL2MXkt1Sgsw%3D%3D

    CAS  Google Scholar 

Download references

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Correspondence to Ahmad R. Bekhradnia.

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Correspondence: Ahmad R. Bekhradnia, Department of Medicinal Chemistry, Mazandaran University of Medical Sciences, Sari, Mazandaran, Iran.

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Bekhradnia, A., Zahir, F. & Arshadi, S. Selective oxidation of organic compounds using pyridinium-1-sulfonate fluorochromate, C5H5NSO3H [CrO3F] (PSFC). Monatsh Chem 139, 521–523 (2008). https://doi.org/10.1007/s00706-007-0720-4

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  • DOI: https://doi.org/10.1007/s00706-007-0720-4

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